Category: 170230-29-2

Electric Literature of 170230-29-2, A common heterocyclic compound, 170230-29-2, name is 4-Bromo-3-ethylbenzonitrile, molecular formula is C9H8BrN, 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.

Description 27; 2-ethyl-2′-fluoro-4-biphenylcarboxylic acid (D27); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (651 mg, 3.10 mmol), 2- fluorophenylboronic acid (867 mg, 6.20 mmol), palladiumtetrakistriphenylphosphine (359 mg, 0.31 mmol) and potassium carbonate (1.29 g, 9.30 mmol) in dimethylformamide (10 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature over a weekend before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-5 % EtOAc in hexane to give a colourless oil (655 mg). This material was added to ethanol (26 ml.) and water (6 ml.) followed by potassium hydroxide (1.62 g, 28.9 mmol) and the mixture heated to 90 0C for 17 h. The solvent was evaporated and the residue partitioned between ethyl acetate and 2M HCI. The organic layer was washed with further HCI before it was dried (phase separator) and concentrated in vacuo to give the title compound as a white solid (648 mg, 2.66 mmol). MS (ES”): Ci5H13FO2 requires 244; found 243 (M-H+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 170230-29-2, A common heterocyclic compound, 170230-29-2, name is 4-Bromo-3-ethylbenzonitrile, molecular formula is C9H8BrN, 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.

Description 27; 2-ethyl-2′-fluoro-4-biphenylcarboxylic acid (D27); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (651 mg, 3.10 mmol), 2- fluorophenylboronic acid (867 mg, 6.20 mmol), palladiumtetrakistriphenylphosphine (359 mg, 0.31 mmol) and potassium carbonate (1.29 g, 9.30 mmol) in dimethylformamide (10 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature over a weekend before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-5 % EtOAc in hexane to give a colourless oil (655 mg). This material was added to ethanol (26 ml.) and water (6 ml.) followed by potassium hydroxide (1.62 g, 28.9 mmol) and the mixture heated to 90 0C for 17 h. The solvent was evaporated and the residue partitioned between ethyl acetate and 2M HCI. The organic layer was washed with further HCI before it was dried (phase separator) and concentrated in vacuo to give the title compound as a white solid (648 mg, 2.66 mmol). MS (ES”): Ci5H13FO2 requires 244; found 243 (M-H+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 170230-29-2, 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 170230-29-2 as follows.

Description 26; 2-ethyl-4-biphenylcarboxylic acid (D26); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (270 mg, 1.30 mmol), phenylboronic acid (302 mg, 2.48 mmol), palladiumtetrakistriphenylphosphine (144 mg, 0.12 mmol) and potassium carbonate (514 mg, 3.72 mmol) in dimethylformamide (4 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature overnight before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-8 % EtOAc in hexane to give a colourless oil (272 mg). This material was added to ethanol (12 ml.) and water (3 ml.) followed by potassium hydroxide (730 mg, 13.0) mmol and the mixture heated to 90 0C overnight. The solvent was evaporated and the residue partitioned between ethyl acetate (40 ml.) and 2M HCI (15 ml_). The organic layer was washed with further HCI (15 ml.) before it was dried (phase separator) and concentrated in vacuo. The resulting solid was purified by MDAP and the product containing fractions concentrated in vacuo. The residue was partitioned between ethyl acetate and 2M HCI. The organic phase was washed with further 2M HCI, dried (phase separator) and evaporated to give the title compound as a white solid (166 mg, 0.73 mmol). MS (ES”): C15H14O2 requires 226; found 225 (M- H+).

According to the analysis of related databases, 170230-29-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts