Hydrochloric Acid → 4-Bromo-N,N-diisopropylbenzamide

Participants

Reaction Steps

To a solution 4-bromobenzoyl chloride (25 g, 114 mmoles) in THF at 0° C. (200 mL) was added triethylamine (63.5 Ml, 456 mmoles) dropwise followed by diisopropylamine (32.5 mL, 228 mmol). The solution was allowed to stir overnight. The next day the reaction mixture was acidified with 1 N HCl and extracted with CH2Cl2. The organic layer was basified with sat. NaHCO3 wash and dried with MgSO4, filtered, and concentrated. Column chromatography on silica gel 100% Hex. to 100% EtOAc provided the desired product as a yellow solid. 1H NMR (600 MHz, CD3OD) δ 7.60 (d, 2H), 7.23 (d, 2H), 3.30 (br s, 1H), 3.29 (br s, 1H), 1.5, (br s, 6H), 1.22 (br s, 6H). LRMS (ESI) calc'd for (C13H19BrNO) [M+H]+, 284.1; found 284.1.

Provenance & Evidence