Thionyl Chloride → alpha-(4-Bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chloride

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Reaction Steps

The crude benzhydryl alcohol (53.2 g, 135 mmol) was dissolved in 1000 mL of dichloromethane and 14.7 mL (202 mmol) of thionyl chloride was added dropwise. The solution was stirred overnight at room temperature and the solvent was removed under vacuum. The crude product was redissolved in 500 mL of toluene and the solvent again was removed under vacuum to eliminate excess thionyl chloride, providing crude α-(4-bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chloride as a dark oil. NMR (200 MHz, CDCl3): δ 0.2 (s,6H); 1.0 (s,9H); 6.0 (s,1H); 6.78 (dd,J1 =1 Hz,J2 =8 Hz,1H); 6.9 (m,2H); 7.2 (t,J=8 Hz,2H); 7.27 and 7.47 (AB q,J=8 Hz,4H).

Provenance & Evidence