Bromine → 2-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

Participants

Reaction Conditions

Reaction Steps

Add p-trifluoromethylpropiophenone (75 g, 360 mmol, 1.0 equiv) to acetic acid (375 mL). Add bromine (18.1 mL, 352 mmol, 0.98 equiv) in acetic acid (375 mL) in a drop-wise fashion over 45 minutes. After completion of the addition, warm the mixture to an internal temperature of 40° C., and stir for 90 minutes. Remove the volatile components under reduced pressure, and dissolve the residue in Et2O (300 mL). Treat with a saturated sodium bicarbonate aqueous solution (4×200 mL) being cautious of vigorous gas evolution. Separate the organic phase, and dry over MgSO4. Remove the solids by filtration; collect the filtrate; and concentrate the filtrate under reduced pressure to give the title compound as a colorless oil which solidifies on standing (93 g, 92.0% yield). 1H NMR (400 MHz, d6-DMSO) δ 8.13 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.3 Hz, 2H), 5.27 (q, J=6.5 Hz, 1H), 1.93 (d, J=6.5 Hz, 3H).

Provenance & Evidence