3-Bromobenzoic acid → 3-bromo-N-(4-(trifluoromethoxy)phenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromobenzoic acid (10 g, 49.7 mmol), thionyl chloride (4.72 mL, 64.7 mmol), and DMF (1.5 mL) in toluene (80 mL) was stirred at 80° C. for 2 h. The mixture was cooled to 0° C., treated dropwise with DIPEA (19.11 mL, 109 mmol) followed by 4-trifluoromethoxyaniline (6.73 mL, 49.7 mmol) and the RM was allowed to warm to RT and stirred overnight. The mixture was diluted with EtOAc (150 mL), washed with 0.5 M HCl (2×100 mL), sat. NaHCO3 (2×100 mL) and brine (100 mL), dried over MgSO4 and the solvent was evaporated off under reduced pressure and the product was crystallized from n-heptane/EtOAc to afford the title compound. LC-MS (Condition 5) tR=1.37 min, m/z=360.1, 362.1 [M+H]+; 1H-NMR (400 MHz, MeOD) δ ppm 7.30 (d, J=8.80 Hz, 2H) 7.47 (t, J=7.95 Hz, 1H) 7.74-7.86 (m, 3H) 7.93 (d, J=7.82 Hz, 1H) 8.13 (s, 1H).

Provenance & Evidence