Dichloromethane → Biphenyl

Participants

Reaction Steps

4-(Chloromethyl)-2-((1R)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl or 4-(chloromethyl)-2-((1S)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl (66.6O or 66.6P). To a stirred solution of (2-((1R)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methanol or (2-((1S)-2,2-dimethylcyclopentyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methanol (66.6AG or 66.6AH) (23.66 g, 72 mmol) in DCM (360 mL, 72 mmol) and DMF (0.56 mL, 7.2 mmol) at 0° C. was added thionyl chloride (11 mL, 144 mmol). Stirring was continued at room temperature for 1 hour. The reaction as then concentrated in vacuo, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield 66.6O or 66.6P as a colorless oil (23.0 g, 92% yield). MS ESI (pos.) m/e: 364.1 (M+H2O)+.

Provenance & Evidence