2,2,2-Trifluoroethanol → HCID 87103607, compound

Participants

Reaction Steps

To a solution of 1.273 g trifluoroethanol in 20 ml dimethylsulfoxide was added 0.463 g sodiumhydride 55% in oil and the mixture was stirred at room temperature for 15 min. To the resulting solution was added a solution of 3.2 g 6-chloro-2-(4-chloro-phenyl)-3-fluoro-pyridine in 10 ml dimethylsulfoxide and the mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with a gradient of heptane to dichloromethane to yield 3.30 g of the title compound as slightly yellow solid. MS (EI): 322.1 and 324.2 (M+H). The product was obtained as 85:15 mixture of F vs Cl substitution products (6-chloro-2-(4-chloro-phenyl)-3-(2,2,2-trifluoro-ethoxy)-pyridine vs. 2-(4-chloro-phenyl)-3-fluoro-6-(2,2,2-trifluoro-ethoxy)-pyridine) that were better separable at the next step.

Provenance & Evidence