Diisopropylamine → 4-Bromo-N,N-diisopropylbenzamide

Participants

Reaction Steps

A mixture of 4-bromobenzoic acid (200 g, 1 mol) and thionyl chloride (300 mL) was refluxed for 3 hours. The mixture was concentrated in vacuo to remove excessive thionyl chloride, and then azeotroped with toluene (3×). The crude residue was dissolved in CH2Cl2 (2 L) and cooled in ice-water bath. To the resulting solution was added dropwise a mixture of triethylamine (330 mL, 2.38 mol) and diisopropylamine (168 mL, 1.19 mol) over 1 hour. The solution was allowed to stir overnight, and then washed with 1N HCl, followed by brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 4-bromo-N,N-diisopropylbenzamide. LRMS calc'd for (C13H18BrNO) [M+H]+, 284; found 284.

Provenance & Evidence