Acetic Acid → HCID 23291929, compound

Participants

Reaction Steps

A solution of 4-bromo-3-methylaniline (5.05 g, 27 mmol) in acetic acid (6.0 mL), acetone (7.0 mL), ethanol (25.0 mL) and water (16.0 mL) was cooled to 0° C. and treated with sodium acetate (7.16 g, mmol). The reaction was stirred 5 minutes and then treated slowly and in several small portions with sodium borohydride (5.15 g, 136 mmol) and the resulting reaction mixture was stirred at 0° C. for 3 hours. The solution was neutralized with NaOH pellets and extracted with ether (2×). The combined organic extracts were washed with brine and dried (Na2SO4). The filtered solution was concentrated under reduced pressure to give the title compound (5.68 g, 92%) as an oil.

Provenance & Evidence