Tag: M.W=200-300

Reference of 330793-38-9, These common heterocyclic compound, 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, 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.

b) 4-Bromo-2-methoxybenzoic acid 4-Bromo-2-methoxybenzonitrile (7.35 g, 35 mmol) was dissolved in dioxane (400 mL). Sodium hydroxide (2.0 N, 200 mL) was added and the suspension was heated at 100° C. for 16 hours. Organic solvent was removed under reduced pressure and the aqueous mixture was filtered and washed with water. The filtrate was neutralized with hydrochloric acid (5.0N) to pH 1. The solid was collected by filtration to give 4-bromo-2-methoxybenzoic acid (3 g, 37percent). 1H NMR (DMSO-d6) delta 3.84(s, 3H), 7.21 (d, J=8.25 Hz, 1H), 7.33 (s, 1H), 7.58 (d, J=8.23 Hz, 1H).

Statistics shows that 4-Bromo-2-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 330793-38-9.

Reference of 70591-86-5, 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. 70591-86-5 name is 3-Bromobenzoylacetonitrile, 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.

A mixture of 3-(3-bromophenyl)-3-oxopropanenitrile (35 g, 156 mmol) and hydrazine hydrate (11.34 mL, 234 mmol) in ethanol (600 mL) was refluxed for 16 h. Mixture was then cooled and concentrated in vacuuo. Crude product was diluted with dichloromethane and stirred for 5 min. Solids were filtered and dried to afford 3-(3-bromophenyl)-1H-pyrazol-5-amine (30 g, 126 mmol, 81 % yield) as off-white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.02 (br. s., 0.4H), 11.66 (br. s., 0.6H), 7.86 (t, J=1.6 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.45 (d, J=6.8 Hz, 1H), 7.37 – 7.18 (m, 1H), 5.78 (br. s., 1H), 5.08 (br. s., 1.2H), 4.68 (br. s., 0.8H). LCMS (M+H) = 240.1.

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

Electric Literature of 120315-65-3, These common heterocyclic compound, 120315-65-3, name is 4-Bromo-3-methoxybenzonitrile, 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.

A mixture of 4-bromo-3-methoxybenzonitrile(lg, 4.72 mmol), 4,4,4′,4′,5,5,5′,5′- octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.796 g, 7.07 mmol), K3P04 (1.157 g, 11.79 mmol) and PdCl2(dppf) CH2C12 adduct (0.207 g, 0.283 mmol) in dioxane (12 mL) was degassed and then heated at 90 C for 3 h. The reaction was cooled to rt and was filtered through a pad of CELITE. The solvent was removed. Normal phase chromatography afforded X-lb as brown oil (1.7 g, 5.76 mmol, 100%). LC-MS (ESI) of the boronic acid m/z: 178.0 [M+H]+.

Statistics shows that 4-Bromo-3-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 120315-65-3.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 92616-49-4, name is 4-Bromo-1-naphthonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C11H6BrN

Under N2 atmosphere, bis(pinacolato)diboron (8.4g, 33mmol), potassium acetate (6.5g, 66mmol) and [1,1?-bis(diphenylphosphine)ferrocene]palladium dichloride (1.2g, 1.76mmol) were respectively added to a solution of compound3-d (5.1g, 22mmol) in dioxane (150mL), the mixture was stirred at 80C for 6hrs. The mixture was evaporatedunder reduced pressure, the residue was filtered through celite, the filtrate cake was washed with dioxane (50mL), thefiltrate was evaporated under reduced pressure. The residue was purified with silica column chromatography (PE:EA =10:1) to give compound 3-c (6 g, yield 97%). LC-MS (ESI): m/z = 280 [M+H]+.

The synthetic route of 92616-49-4 has been constantly updated, and we look forward to future research findings.

Related Products of 330793-38-9,Some common heterocyclic compound, 330793-38-9, name is 4-Bromo-2-methoxybenzonitrile, molecular formula is C8H6BrNO, 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 suspension of 5.349g (lOOmmol) of ammonium chloride in 200mL of toluene was dropped lOOmL (lOOmmol) of IM-triethylaluminum/hexane, and the mixture was stirred for 1.5 hours at room temperature. Then, to this mixture was added 8.48g (40mmol) of the compound obtained in the Manufacturing Example 2, and the mixture was stirred for 24 hours at 80°. After the reaction mixture was cooled with ice water, 30g of silica gel and 300mL of chloroform were added to the mixture and the mixture was stirred for 30 minutes under the roomtemperature. The mixture was filtrated with Celite.(R). and the residue was washed with 400mL of methanol. The organic layer was concentrated and 200mL of chloroform/methanol (9/1) solution was added to the residue. The mixture was filtrated and the filtrate was concentrated and the residue was washed sequentially with ether to give 3.47g (33percent) of the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methoxybenzonitrile, its application will become more common.

Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, 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 36282-26-5, name: 2-Bromo-4-fluorobenzonitrile

5,4′-Difluoro-biphenyI-2-carbonitrie (CAB06058)A mixture of 2-bromo-4-fiuorobenzinitrile (5.0 g, 25.0 mmol), 4-fiuorophenylboronic acid (3.85 g,27.5 mmol), dimethoxyethane (30 rtiL) and 2M Na2CO3 (40 mL) was heated to reflux before Pd2(dba)3 (0.10 g) was added and heating was continued for 5 hours. After cooling to room temperature CHCl3 (50 mL) was added to and the mixture was filtered (celite). The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography [SiO2, CHCl3] followed by recrystallisation from CHCl3/n-hexane to afford CAB06Theta58 (4.03 g, 71%) as colorless needles. Mp. 111-113 C; 1H NMR (400 MHz, CDCl3) delta 7,12-7.23 (m, 4H)3 7.50-7.56 (m, 2H), 7,76 (dd, J = 8.6, 5.4 Hz, IH); LRMS (ES+): m/z 416.0 (100%, [M+H]+); HRMS (ES+) calcd for Ci3H8F2N [M+H]+: 216,0619, found 216.0613; Anal, Calcd for Cj3H7F2N: C, 72.56; H3 3.28; N, 6.51. Found C, 72.4; H, 3.28; N3 6.55.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1953-99-7, These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

(i) Preparation of 1,2-dicyano-3,4,5,6-tetraphenoxybenzene A mixture of 1,2-dicyano-3,4,5,6-tetrachlorobenzene (50 parts), phenol (106 parts), potassium carbonate (104 parts) and dimethylformamide (200 parts) was stirred and heated at 70¡ã C. for 2 hours before pouring into water (500 parts). The aqueous mixture was extracted with chloroform (2*300 parts). The chloroform extract was washed with a 5percent aqueous solution of sodium hydroxide (2*250 parts) and then with water (2*250 parts). The chloroform extract was dried over anhydrous magnesium sulphate, filtered and the chloroform was removed by distillation under reduced pressure to leave a brown oil. The brown oil was dissolved in hot butan-1-ol and allowed to cool slowly. 1,2-Dicyano-3,4,5,6-tetraphenoxybenzene (62.2 parts, 67percent) was obtained as a pale yellow solid m.p. 149¡ã-151¡ã C.

Statistics shows that 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile is playing an increasingly important role. we look forward to future research findings about 1953-99-7.

Reference:
Patent; Zeneca, Limited; US5486274; (1996); A;; ; Patent; Zeneca Limited; US5484915; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: nitriles-buliding-blocks

Step 1 : Synthesis of 4-cyano-2,6-dimethylphenylboronic acid pinacol ester First, 5.0 g (24 mmol) of 4-bromo-3,5-dimethylbenzonitrile, 7.3 g (29 mmol) of bis(pinacolato)diboron, 8.4 g (86 mmol) of potassium acetate, and 120 mL of dimethyl sulfoxide (DMSO) were put into a three-neck flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 0.20 g (0.24 mmol) of [l, l’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct and 0.20 g (0.48 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and the mixture was heated and stirred at 90 C for 7 hours. To this mixture were further added 0.20 g (0.24 mmol) of [l,l’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct, 0.20 g (0.48 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 3.5 g (14 mmol) of bis(pinacolato)diboron were further added to, and the mixture was heated and stirred at 100 C for 17 hours to be reacted. Water was added to the reacted solution to separate the solution into an organic layer and an aqueous layer, and the aqueous layer was subjected to extraction with toluene. A solution obtained by combining the organic layer and the solution of the extract was washed with water and saturated saline, and anhydrous magnesium sulfate was added thereto for drying. The obtained mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was purified by flash column chromatography. As developing solvents, first, a mixed solvent of toluene and ethyl acetate in a ratio of 10: 1 (v:v) was used, and then a mixed solvent of toluene and ethyl acetate in a ratio of 5: 1 (v:v) was used. The obtained fraction was concentrated to give a solid. This solid was washed with toluene and hexane, so that 3.5 g of a white solid was obtained in a yield of 57 %. The obtained white solid was identified as 4-cyano-2,6-dimethylphenylboronic acid pinacol ester by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-9) below.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; SEO, Satoshi; WATABE, Takeyoshi; INOUE, Hideko; YAMADA, Yui; MITSUMORI, Satomi; TAKAHASHI, Tatsuyoshi; HARA, Tomoka; (444 pag.)WO2016/203350; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 79463-77-7, These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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.

Diphenyl N-cyanocarbonimidate [79463-77-7] (200 mg, 0.81 mmol, 97 mass%) and 4- aminomorpholine [4319-49-7] (100 mg, 0.98 mmol) were dissolved in DCM (2 mL) and 2-propanol (1.57 g, 26.1 mmol) and DIPEA (159 mg, 1.22 mmol) were added. The reaction mixture was stirred at r.t. for ~1 h before concentrating in vacuo. The crude residue was purified by flash column chromatography on silica (gradient elution with 15-100% EtOAc/hexane) to afford the title compound (170 mg, 85%) as a white solid. dH (300 MHz, DMSO -d6) 10.39 (s, 1H), 7.42 (t, J 7.8 Hz, 2H), 7.28 (t, J 7.4 Hz, 1H), 7.23 – 7.08 (m, 2H), 3.68 (s, 4H), 2.89 (s, 4H). INTERMEDIATES 222 and 223

Statistics shows that Diphenyl N-cyanocarbonimidate is playing an increasingly important role. we look forward to future research findings about 79463-77-7.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 1483-55-2 as follows. Recommanded Product: 2-Bromo-5-(trifluoromethyl)benzonitrile

To a solution of 2-bromo-5-(trifluoromethyl)benzonitrile (10.0 g, 40 mmol) in dichloromethane (100 mL) was dropwise added a 1.0 M solution of diisobutylaluminum hydride in hexane (48 mL). The resulting solution was stirred under nitrogen at ambient temperature for 1 h and was then diluted by addition of ether (100 mL). After cooling in an ice bath, a 3 N solution of HCl was carefully added, and the mixture was vigorously stirred at ambient temperature for 15 min. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting oil was purified by flash chromatography (5% EtOAc/hexane) affording 5 g of 2-bromo-5-trifluoromethylbenzaldehyde. 1H NMR (CDCl3) delta 10.39 (s, 1H), 8.18 (d, J=2 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.70 (dd, J=8.5 Hz, 2 Hz, 1H).

According to the analysis of related databases, 1483-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts