Triethylamine → (+/-)-N-[2,6-bis(1-Methylethyl)phenyl]-alpha-bromobenzeneacetamide

Participants

Reaction Conditions

Reaction Steps

The α-bromophenylacetylchloride (21.0 g, 89.7 mmol) was added slowly via pipet to a cooled (0° C.) solution of 2,6-diisopropylaniline (15.9 g, 89.7 mmol) and triethylamine (12.5 mL, 89.7 mmol) in ethyl acetate (1600 mL). The resulting slurry was warmed (25° C.) then stirred (1 hour). The resulting mixture was diluted with ethyl acetate (1000 mL) and dichloro methane (500 mL), then washed with water (1000 mL), with 0.5N aqueous HCl (2×1000 mL), with saturated aqueous sodium bicarbonate (1×600 mL), with brine (1×600 mL), then dried (MgSO4) and concentrated to a solid. The solid was recrystallized from ethyl acetate to yield 27.2 g (81.0%) of (±)-N-[2,6-bis(1-Methylethyl)phenyl]-α-bromobenzeneacetamide as a white solid, mp 207°-209.5° C.

Provenance & Evidence