Triethylsilane → 4-Bromo-2-(4-(bromomethyl)benzyl)-1-chlorobenzene

Reaction equation

[SiH](CC)(CC)CC.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:25])=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:24])=[CH:19][CH:18]=2)=O)[CH:14]=1.C(S(O)(=O)=O)(F)(F)F>C(O)(C(F)(F)F)=O>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:25])=[C:13]([CH2:15][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:24])=[CH:19][CH:18]=2)[CH:14]=1

Participants

Procedure

To a stirred solution of Et3SiH (17 mL) and (5-bromo-2-chlorophenyl)(4-(bromomethyl)phenyl)methanone (intermediate AH) (20.75 g, 54 mmol) in TFA (100 mL) at 30° C. was added CF3SO3H (0.05 mL). Within a few minutes the temperature of the solution increased causing it to reflux violently. After 3 h, the volatiles were removed under reduced pressure. The residue was poured into brine and extracted 3× with ethyl acetate. The combined organic layers were washed 3× with H2O, 2× with aqueous Na2SO4 and 2× with brine, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography to obtain pure intermediate AI (15.5 g).