Ethyl Acetate → (2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

Participants

Reaction Steps

To a solution of methyl 2-bromo-5-chloro-4-(4-ethylbenzoyl)benzoate (7.64 g, 20 mmol) in 2,2,2-trifluoroacetic acid (38 mL) was added to triethylsilane (5.88 mL, 40 mmol) under argon. After it was stirred for 10 min at room temperature, trifluoromethanesulfonic acid (0.1 mL) was added. The reaction temperature was raised from 26° C. to reflux. After stirring for 2 hours, TLC (petroleum ether:ethyl acetate=6:1, Rf=0.7) showed the reaction was complete. The reaction mixture was evaporated and the residue was dissolved in ethyl acetate (150 mL). The organic layer was washed 2× with H2O, 2× with NaHCO3, and 2× with brine, dried over anhydrous Na2SO4. Concentration under reduced pressure provided the title compound as a white solid. Yield: 7.2 g (100%). 1H NMR (CDCl3, 300 MHz) δ 7.85 (s, 1H), 7.44 (s, 1H), 7.17 (s, 1H), 7.14 (s, 1H), 7.10 (s, H), 7.07 (s, 1H), 4.05 (s, 2H), 3.92 (s, 3H), 2.63 (q, J=7.8 Hz, 2H), 1.24 (t, J=7.8 Hz, 3H).

Provenance & Evidence