Author: Jessica.F

Electric Literature of 198633-76-0,Some common heterocyclic compound, 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, molecular formula is C8H6FN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step A: 3-bromo-6-fluoro-2-methylbenzonitrile (Method A): Commercially available 2-fluoro-6-methylbenzonitrile (Apollo Scientific, 15.0 g, Ill mmol) was dissolved in triflic acid (75 mL)at 0 C then NBS (20.7 g, 117 mmol) was added. The reaction mixture was stirred at RT for 1 hthen poured into ice water and extracted twice with DCM. The organic layer was washed with brine, dried over Na2S04, then filtered and evaporated to dryness to yield 3-bromo-6-fluoro-2-methylbenzonitrile: LC-MS: M+ 1 = 214, 216.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-6-methylbenzonitrile, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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Synthetic Route of 874-89-5,Some common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Hydroxymethyl)benzonitrile, its application will become more common.

Reference:
Article; Farhadi, Saeed; Jahanara, Kosar; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 3; (2014); p. 368 – 375;,
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Related Products of 22972-63-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 22972-63-0 name is 2-(3,5-Dimethoxyphenyl)-2-methylpropanenitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-(3,5-dimethoxyphenyl)-2-methylpropanenitrile (10 g, 46.9 mmol, Eq: 1.00) was dissolved in MTBE (50 mL). The clear solution was cooled to 10C and 1 M DIBAL-H in heptane (56.3 mL, 56.3 mmol, Eq: 1.2) was added dropwise over 30 min. The reaction mixture was warmed to 20C over 30 min. After 2 h at 20C, the reaction mixture was added to a cold (0C) mixture of heptane (50 mL) and 2 M aqueous HC1 (100 mL). The water phase was separated and extracted with heptane (50 mL). The organic phases were washed twice sequentially with 2 M aqueous HC1 (2×50 mL), then half saturated aqueous NaHCC>3 (50 mL) and half saturated aqueous NaCl (50 mL). The organic phases were combined, dried over Na2S04, filtered and concentrated under reduced pressure to give 10.3 g of the crude title compound as an oil (97a% GC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3,5-Dimethoxyphenyl)-2-methylpropanenitrile, and friends who are interested can also refer to it.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; ADAM, Jean-Michel; DOTT, Pascal; HOHLER, Marcus; BURGER, Tanja; TAGLIENTE, Orazio; MISCHLER, Ernst; (49 pag.)WO2018/87767; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 621-50-1, Quality Control of 2-(3-Nitrophenyl)acetonitrile

(3-Nitro-phenyl)-acetonitrile (1.51 g, 9.31 mmol), dimethoxymethyl-dimethyl-andine (6.2 mL, 46.5 mmol) in xylene (30 mL) are stirred at reflux for 1 hour. After adding hexane (20 mL), the reaction mixture is cooled at 0C. Precipitating material is filtered-off to give compound of Stage 52.1 as brown solid (1.76 g, 8.19 mmol ; 88%); ES-MS: M+H = 218. 1; HPLC: tRet = 2.24 minutes. 1H-NMR (300 MHz, DMSO-d6) : 8.10-8. 05 (m, 1H), 7.90-7. 85 (m, 1H), 7.75-7. 72 (m, 1H), 7.70 (s, 1H), 7.65-7. 60 (m, 1H), 3.30 (s, 6H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(3-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); A1;,
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Application of 21803-75-8, The chemical industry reduces the impact on the environment during synthesis 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

Thionylchloride (15 mL) was dropped into water (60 mL) with stirring and cooling sothat the temperature did not rise above -5C. Copper(I) chloride (19 mg) wasthen added. In parallel, 4-amino-3-chlorobenzonitrile (1.50g, 9.83 mmol) wasdissolved in cone. HCl (30 mL), cooled to -5C whereupon a solution of sodiumnitrite (746 mg, 10.8 mmol) in water (15 mL) was added . After completeaddition the solution of diazonium salt was added in over 2 mins to the firstsolution, both at -5 to OoC (gas evolution was observed) and a foam formed ontop of the solution. The temperature was allowed to come to room temperatureand the aqueous phase was then extracted with DCM (3 x 70 ml). The combinedorganic phase was washed with brine (5 mL), dried (Na2SC>4), themixture filtered and the filtrate evaporated to dryness to afford a yellowsolid containing the title compound (1.88 g, 88%); ‘H NMR (500 MHz, CDC13)delta 7.83 (dd, IH), 7.97 (d, IH), 8.31 (d, IH).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6574-97-6 as follows. Recommanded Product: 6574-97-6

EXAMPLE 56C 3-Amino-2-carbomethoxy-7-chloro-benzthiophene The product from Example 56B (1.7 g, 10 mmol) was treated with 1 eq of methyl thioglycolate and 1 eq sodium carbonate in methanol as described in Example 41A to give after chromatography (4:1 hexane/EtOAc) the title compound in 12percent yield. 1H NMR (300 MHz, CDCl3) d 3.81 (s, 3H), 5.90 (bs, 2H), 7.34 (t, J=8 Hz, 1H), 7.48 (dd, J=8.1 Hz, 1H), 7.56 (dd, J=8,1 Hz, 1H). MS (DCI/NH3) m/e 259 (M+NH4)+.

According to the analysis of related databases, 6574-97-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US5597823; (1997); A;,
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Application of 103146-25-4, These common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of Racemic cyanodiol (300g, 0.88 moles) in isopropyl alcohol (1800 ml) at 25-35C (+)-Di-p-toluoyl-D-tartaric acid (169.2g, 0.44 mole) was added. The reaction mixture was then heated and maintained at 60-70 C for lhour. After maintaining was over the reaction mass was cooled and maintained at 28- 32 C for 2-4 hours. The precipitated solid was then filtered, washed with isopropyl alcohol (300 ml) and suck dried for 30minutes. The filtrate was preserved for the recovery of Racemic cyanodiol and (+)-Di-p-toluoyl-D-tartaric acid. The obtained wet cake of (S)-cyanodiol – (+)-DPTTA was suspended in isopropyl alcohol (1200 ml), heated and maintained at 55-65C for 60 minutes. After maintaining was over the reaction mass was cooled to 28-32C where it was maintained for 60 minutes. The precipitated solid was then filtered, washed with isopropyl alcohol (300 ml) and finally dried under vacuum at 60-70 C which provided the title compound (VI) as a white solid. The obtained filtrate was combined with the earlier obtained filtrate for the recovery of Racemic cyanodiol and (+)-Di-p-toluoyl-D-tartaric acid. Yield: 145g (61.96% by Theory) Purity by HPLC: 99.71% Chiral Purity: S-Isomer – 99.59% R-Isomer – 0.41%

Statistics shows that 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 103146-25-4.

Reference:
Patent; IPCA LABORATORIES LIMITED; REGURI, Buchi Reddy; PRASAD, Ashok; RAWAT, Ajay Singh; RAJPUT, Sandip; SANTAN, Rohit B; (36 pag.)WO2017/9866; (2017); A1;,
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Some common heterocyclic compound, 10412-93-8, name is N-Benzyl-2-cyanoacetamide, molecular formula is C10H10N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 10412-93-8

General procedure: (E)–aryl–cyanoacrylamides 2 was prepared according to literature procedure.2 General procedure for 2a. To a solution of benzaldehyde (10 mmol 1.0 equiv), pyrrolidine (2 mmol, 20 mol %) in ethanol (20 mL) was added N-benzyl-2-cyanoacetamide (10 mmol, 1.0 equiv). The reaction mixture was stirred at room temperature until the reaction was complete (monitored by TLC), the solvent was removed under reduced pressure. The crude reaction mixture was purified through flash column chromatography on silica gel to afford 2a. 1H NMR (CDCl3, 400 MHz): delta (ppm) 8.68 (s, 1H), 7.78-7.74 (m, 1H), 7.70 (dd, J = 7.6, 1.4 Hz, 1H), 7.43 (t, J = 7.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz): delta (ppm) 167.9, 154.4, 137.8, 131.0, 126.4, 118.8, 115.6.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10412-93-8, its application will become more common.

Reference:
Article; Nie, Xufeng; Wang, Yachuan; Yang, Lijun; Yang, Zaijun; Kang, Tairan; Tetrahedron Letters; vol. 58; 31; (2017); p. 3003 – 3007;,
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Synthetic Route of 134227-45-5,Some common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, molecular formula is C7H2F3N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(Methylsulfinyl) (methylthio) methane (7.26g, 0.0584 mol) was dissolved in 100 mL of dry THF under argon and was cooled [TO-78C.] Butyllithium in hexane (16 mL 1. 6M, 0.0256 mol) was added dropwise with stirring. The mixture was stirred for 15 min. Meanwhile, a solution of 3,4, 5-trifluorobenzonitrile (4.0 g, 0.025 mmol) in 100 [ML] of dry THF was cooled to-78C under argon and the former solution was added through a cannula to the latter solution over a period of 35 min. After 30 min, the cooling bath was removed and when the reaction had reached room temperature it was poured into 400 mL of water. The THF was evaporated and the remaining aqueous layer was extracted three times with diethyl ether. The combined ether phase was washed with water, dried [(NA2SO4)] and evaporated. Yield: 2.0 g (30%). ‘H NMR (500 MHz, [CDC13)] 8 7.4-7. 25 (m, 2H), 5.01 (s, [1H,] diasteromer), 4.91 (s, [1H,] diasteromer), 2.88 (s, 3H, diasteromer), 2.52 (s, 3H, diasteromer), 2.49 (s, 3H, diasteromer), 2.34 (s, 3H, diasteromer), 1.72 (broad, [1H)]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trifluorobenzonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2003/101956; (2003); A1;,
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Reference of 906673-45-8,Some common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

40.0 g (131 mmol) of 4-(4-bromo-3-hydroxymethyl-phenoxy)-benzonitrile of formula (II), prepared as described in Example 3, are added under nitrogen to 400 mL THF and 23.8 g (236 mmol) of triethylamine in a previously anhydrified flask. The solution is cooled down to 0 C. and 16.9 g (157 mmol) of trimethylsilyl chloride are added maintaining the temperature below 15 C. After completion of the addition, the mixture is allowed to reach room temperature. 50 mL of toluene and 100 mL of water are added and the phases are separated. The organic phase is washed with a saturated NaCl solution and evaporated to dryness under reduced pressure to obtain 49.4 g of 4-(4-bromo-3-trimethylsilanoxymethyl)-benzonitrile of formula (II) as a solid with a yield of 98%. The obtained product is used in the next step any without further purification. 1H-NMR (CDCl3, 300 MHz) delta (ppm): 7.63-7.60 (2H, m) 7.52 (1H, d, J=8.4 Hz), 7.22 (1H, m) 7.03-7.00 (2H), 6.85-6.80 (1H, m) 4.69 (2H, s), 0.17 (9H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, its application will become more common.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; Santillo, Niccolo’; Attolino, Emanuele; Brenna, Davide; Vladiskovic, Chiara; Lombardo, Alessandro; Razzetti, Gabriele; US2019/241585; (2019); A1;,
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