Methylamine → 5-bromo-N,2-dimethylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methylbenzoic acid (2.325 mmol, 0.5 g) in dichloromethane (25 mL) under nitrogen was added N,N-diisopropylethylamine (0.75 g, 5.8 mmol). Reaction then cooled in an ice bath to 2° C. and the yellow solution treated with 2M methylamine in tetrahydrofuran (3.49 mL, 6.98 mmol) over 5 minutes, followed by 1-propanephosphonic acid cyclic anhydride as a 50% wt solution in ethyl acetate (2.08 mL, 3.49 mmol) added dropwise. The ice bath was then removed and stirring continued overnight. The mixture was purified on silica (15 g column on Isolera 4) eluting with 0-5% methanol in dichloromethane to afford 5-Bromo-N,2-dimethylbenzamide (0.5 g, 2.2 mmol).

Provenance & Evidence