3-bromo-N-propan-2-ylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (16.5 g, 435 mmol) was added slowly over 2 hours to a mixture of 3-bromoaniline (10 g, 58.13 mmol), ethanol (58 mL), acetic acid (50 mL, 866.1 mmol), water (140 mL), acetone (35 mL, 482.5 mmol), and sodium acetate (15.8 g, 116.2 mmol). The solution was stirred at 0° C. for 3 hours. The reaction mixture was poured into 1:1 mixture of ether and hexane containing 2N KOH. The layers were separated and the aqueous layer was extracted with ether/hexane (1:1). The combined organic layers were washed once with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31) to give the title compound (23.10 g, 93% as an oil: The layers were separated the aqueous layer was extracted with ether/hexane (1:1) The combined organic layers were washed once with water and brine dried with MgSO4 filtered concentrated under reduced pressure The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (16.5 g, 435 mmol) was added slowly over 2 hours to a mixture of 3-bromoaniline (10 g, 58.13 mmol), ethanol (58 mL), acetic acid (50 mL, 866.1 mmol), water (140 mL), acetone (35 mL, 482.5 mmol), and sodium acetate (15.8 g, 116.2 mmol). The solution was stirred at 0° C. for 3 hours. The reaction mixture was poured into 1:1 mixture of ether and hexane containing 2N KOH. The layers were separated and the aqueous layer was extracted with ether/hexane (1:1). The combined organic layers were washed once with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31) to give the title compound (23.10 g, 93% as an oil: The layers were separated the aqueous layer was extracted with ether/hexane (1:1) The combined organic layers were washed once with water and brine dried with MgSO4 filtered concentrated under reduced pressure The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (16.5 g, 435 mmol) was added slowly over 2 hours to a mixture of 3-bromoaniline (10 g, 58.13 mmol), ethanol (58 mL), acetic acid (50 mL, 866.1 mmol), water (140 mL), acetone (35 mL, 482.5 mmol), and sodium acetate (15.8 g, 116.2 mmol). The solution was stirred at 0° C. for 3 hours. The reaction mixture was poured into 1:1 mixture of ether and hexane containing 2N KOH. The layers were separated and the aqueous layer was extracted with ether/hexane (1:1). The combined organic layers were washed once with water and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31) to give the title compound (23.10 g, 93% as an oil: The layers were separated the aqueous layer was extracted with ether/hexane (1:1) The combined organic layers were washed once with water and brine dried with MgSO4 filtered concentrated under reduced pressure The residue was purified by silica gel chromatography (10% ethyl acetate in hexane, Rf=0.31)