Dimethylamine → 2,3-difluoro-5-iodo-N,N-dimethyl-benzamide

Participants

Reaction Steps

2,3-Difluoro-5-iodo-benzoic acid (7.20 g, 25.35 mmol), di-iso-propylethylamine (4.5 ml, 25.83 mmol), trimethylacetyl chloride (3.2 ml, 25.98 mmol), and dichloromethane (100 ml) were combined and stirred at room temperature for 1 hour. Dimethylamine (2 M in tetrahydrofuran, 22.0 ml, 44.00 mmol) was added to the reaction, and the combined mixture was stirred for an addition 18 hours at room temperature. The mixture was concentrated in vacuo, and the crude product was purified by flash chromatography on silica gel (0 to 40% ethyl acetate in hexanes) to afford 7.17 g (91%) of 2,3-difluoro-5-iodo-N,N-dimethyl-benzamide. 1H-NMR (250 MHz, d6-DMSO) δ 8.02-7.90 (m, 1H), 7.60-7.54 (m, 1H), 2.99 (s, 3H), 2.84 (s, 3H); LCMS m/z 400.0 (M+H+); MS: m/z 312.0 (M+H+).

Provenance & Evidence