4-(Trifluoromethyl)aniline → 2-Azido-4-bromo-N-(4-trifluoromethylphenyl)-benzamide

Participants

Reaction Steps

The product of Step 1 (6.4 g, 0.026 mol) was heated in SOCl2 (30 mL) at reflux for 2 h. The excess reagent was then evaporated and chased with toluene (2×10 mL). The residue was dissolved in dry CH2Cl2 (20 mL) and added dropwise to a solution of 4-(dimethylamino)pyridine (3.2 g, 0.026 mol) and 4-aminobenzotrifluoride (4.3 g, 0.026 mol) in CH2Cl2 (40 mL) cooled in ice. When addition was complete (10 min), the mixture was stirred and warmed to room temperature over 1 h, then washed with 2N HCl (15 mL), 2N Na2CO3 solution (15 mL), brine (10 mL), dried (MgSO4) and concentrated to give 8.4 g (84% yield) of product as a buff solid. 1H NMR (360 MHz, CDCl3): 7.40 (1H, d, J 1.4 Hz), 7.44 (1H, dd, J 1.4 and 8.5 Hz), 7.63 (2H, d, J8.5 Hz), 7.80 (2H, d, J 8.5 Hz), 8.14 (1H, d, J 8.5 Hz).

Provenance & Evidence