Trifluoroacetic acid → 4-Bromo-2-fluoro-1-(1-methylethyl)benzene

Participants

Reaction Steps

To a solution of 2-(4-bromo-2-fluorophenyl)propan-2-ol (7.6 g, 32.8 mmol) dissolved in anhydrous CH2Cl2 (300 mL) at 25° C. was added triethylsilane (7.8 mL, 49.1 mmol), followed by trifluoroacetic acid (25 mL, 328 mmol). The resulting solution was stirred at that temperature for 45 min. The solvent was removed in vacuo and the residue was purified by flash column chromatography (0-10% EtOAc in hexanes) to give the desired product (5.7 g, 80% yield). 1H NMR (CDCl3, 400 MHz) δ: 1.23 (d, J=6.82 Hz, 3H), 3.15-3.22 (m, 1H), 7.11 (t, J=8.08 Hz, 1H), 7.17 (dd, J=9.85, 1.77 Hz, 1H), 7.22 (d, J=8.34 Hz, 1H).

Provenance & Evidence