1-(4-bromo-2,6-difluorophenyl)ethanamine

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

Procedure: To a mixture of 1-(4-bromo-2,6-difluorophenyl)ethanone (450 mg, 0.91 mmol), titanium isopropoxide (1.14 mL, 4.61 mmol) in ethanol (10 mL) was added a solution of 2M ammonia in ethanol (4.8 mL, 9.6 mmol), and the resulting mixture was stirred at room temperature. After 18 hours, sodium borohydride (115 mg, 3.48 mmol) was added and stirring was continued at room temperature for three hours. The reaction mixture was poured into a 2M aqueous ammonium hydroxide solution (100 mL) then filtered. The filtrate was extracted with ethyl acetate (3×50 mL), and the combined extract was washed with water (100 mL), then brine (100 mL), dried over sodium sulfate, filtered and concentrated to give 1-(4-bromo-2,6-difluorophenyl)ethanamine (236 mg, 62% yield), MS (EI) for C8H8BrF2N: 237 (MH+). stirring was continued at room temperature for three hours then filtered The filtrate was extracted with ethyl acetate (3×50 mL) the combined extract was washed with water (100 mL) brine (100 mL), dried over sodium sulfate filtered concentrated

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

Procedure: To a mixture of 1-(4-bromo-2,6-difluorophenyl)ethanone (450 mg, 0.91 mmol), titanium isopropoxide (1.14 mL, 4.61 mmol) in ethanol (10 mL) was added a solution of 2M ammonia in ethanol (4.8 mL, 9.6 mmol), and the resulting mixture was stirred at room temperature. After 18 hours, sodium borohydride (115 mg, 3.48 mmol) was added and stirring was continued at room temperature for three hours. The reaction mixture was poured into a 2M aqueous ammonium hydroxide solution (100 mL) then filtered. The filtrate was extracted with ethyl acetate (3×50 mL), and the combined extract was washed with water (100 mL), then brine (100 mL), dried over sodium sulfate, filtered and concentrated to give 1-(4-bromo-2,6-difluorophenyl)ethanamine (236 mg, 62% yield), MS (EI) for C8H8BrF2N: 237 (MH+). stirring was continued at room temperature for three hours then filtered The filtrate was extracted with ethyl acetate (3×50 mL) the combined extract was washed with water (100 mL) brine (100 mL), dried over sodium sulfate filtered concentrated

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

Procedure: To a mixture of 1-(4-bromo-2,6-difluorophenyl)ethanone (450 mg, 0.91 mmol), titanium isopropoxide (1.14 mL, 4.61 mmol) in ethanol (10 mL) was added a solution of 2M ammonia in ethanol (4.8 mL, 9.6 mmol), and the resulting mixture was stirred at room temperature. After 18 hours, sodium borohydride (115 mg, 3.48 mmol) was added and stirring was continued at room temperature for three hours. The reaction mixture was poured into a 2M aqueous ammonium hydroxide solution (100 mL) then filtered. The filtrate was extracted with ethyl acetate (3×50 mL), and the combined extract was washed with water (100 mL), then brine (100 mL), dried over sodium sulfate, filtered and concentrated to give 1-(4-bromo-2,6-difluorophenyl)ethanamine (236 mg, 62% yield), MS (EI) for C8H8BrF2N: 237 (MH+). stirring was continued at room temperature for three hours then filtered The filtrate was extracted with ethyl acetate (3×50 mL) the combined extract was washed with water (100 mL) brine (100 mL), dried over sodium sulfate filtered concentrated