Triethylsilane → 4-Bromo-2-(4-chlorobenzyl)-1-methylbenzene

Participants

Reaction Conditions

Reaction Steps

(5-Bromo-2-methylphenyl)(4-chlorophenyl)methanone (2, 37.0 g, 121 mmol) and triethylsilane (77.3 mL, 484 mmol) were dissolved in 300 mL of CH3CN and cooled to 0° C. BF3OEt2 (91 mL, 726 mmol) was added and the reaction was heated to 60° C. for 2 hours. GCMS was used to monitor the reaction. Upon completion, the reaction was cooled to 0° C. and quenched with 500 mL saturated aqueous NaHCO3. The aqueous phase was extracted twice with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and the solvent removed in vacuo. The crude solid was slurried in 20% EtOAc/hexanes and passed over a silica plug to remove residual salts. Concentration of the filtrate provided the title compound as a white solid (22.0 g, 62% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.22 (d, J=2.0 Hz, 1 H), 7.21-7.31 (m, 3 H), 7.04 (d, J=8.3 Hz, 2 H), 7.04 (d, J=8.1 Hz, 2 H), 3.91 (s, 2 H), 2.17 (s, 3 H). GCMS (CH4—Cl) [M+H]+=295.

Provenance & Evidence