2-bromo-4-hydroxybenzonitrile

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-hydroxy-benzonitrile (Intermediate 7, 2000 mg, 10.1 mmol) in DCM (50 mL) and THF (10 mL), at 0° C., diisobutylaluminum hydride 1M in toluene (20.2 ml, 20.2 mmol) was slowly added (10 min) and the reaction mixture was stirred at the same temperature for 1 hour. Then 40 ml of HCl 2M were added and the reaction mixture was warmed at 40° C. for 30 minutes. After cooling ethyl acetate (100 ml) was added and two phases were separated. The organic layer was washed with brine (3×100 ml) dried over sodium sulphate and concentrated under vacuum to give the title compound (1950 mg) which was used in the next step without further purification. was added two phases were separated The organic layer was washed with brine (3×100 ml) dried over sodium sulphate concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-fluoro-benzonitrile (2000 mg, 9.9995 mmol) in DMF (20 mL), potassium trimethylsilanolate (2565.7 mg, 19.999 mmol) was added portionwise and the reaction mixture stirred at room temperature for 1 h. The mixture was diluted with ethyl acetate (100 ml), washed with an aqueous saturated solution of ammonium chloride (100 ml) and brine (3×100 ml), dried over sodium sulphate and concentrated under vacuum to give the title compound (2000 mg) which was used in the next step without purification. washed with an aqueous saturated solution of ammonium chloride (100 ml) and brine (3×100 ml) dried over sodium sulphate concentrated under vacuum

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-hydroxy-benzonitrile (Intermediate 7, 2000 mg, 10.1 mmol) in DCM (50 mL) and THF (10 mL), at 0° C., diisobutylaluminum hydride 1M in toluene (20.2 ml, 20.2 mmol) was slowly added (10 min) and the reaction mixture was stirred at the same temperature for 1 hour. Then 40 ml of HCl 2M were added and the reaction mixture was warmed at 40° C. for 30 minutes. After cooling ethyl acetate (100 ml) was added and two phases were separated. The organic layer was washed with brine (3×100 ml) dried over sodium sulphate and concentrated under vacuum to give the title compound (1950 mg) which was used in the next step without further purification. was added two phases were separated The organic layer was washed with brine (3×100 ml) dried over sodium sulphate concentrated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-bromo-4-fluoro-benzonitrile (2000 mg, 9.9995 mmol) in DMF (20 mL), potassium trimethylsilanolate (2565.7 mg, 19.999 mmol) was added portionwise and the reaction mixture stirred at room temperature for 1 h. The mixture was diluted with ethyl acetate (100 ml), washed with an aqueous saturated solution of ammonium chloride (100 ml) and brine (3×100 ml), dried over sodium sulphate and concentrated under vacuum to give the title compound (2000 mg) which was used in the next step without purification. washed with an aqueous saturated solution of ammonium chloride (100 ml) and brine (3×100 ml) dried over sodium sulphate concentrated under vacuum