4-Chlorobenzaldehyde → 2,2-Difluoro-1-phenyl-3-(4'-chlorophenyl)-1,3-propanediol

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Reaction Steps

Into the mixture of PhSO2CF2CH(OH)Ph (120 mg, 0.4 mmol) and 4-chlorobenzaldehyde (113 mg, 0.8 mmol) in DMF (3 mL) at −50° C., was added t-BuOK (90 mg, 0.8 mmol) in 2 mL DMF. The reaction mixture was stirred at −50° C. to RT overnight. The reaction was then quenched with cold NaCl aqueous solution, followed by extraction with Et2O (20 mL×3). After drying over MgSO4 and solvent removal, the product 2,2-Difluoro-1-phenyl-3-(4′-chlorophenyl)-1,3-propanediol was obtained by chromatography as a white solid, 76% yield. For anti-isomer: 1H NMR (CDCl3): δ 3.22 (m, 2H); 5.04 (td, J=11.0 Hz, 2H); 7.36 (m, 9H). 13C NMR (CDCl3): δ 72.9 (t, J=29 Hz); 73.8 (t, J=29 Hz); 118.7 (t, J=259 Hz); 127.6; 128.6; 129.0; 134.3; 134.8. 19F NMR(CDCl3): δ −118.2˜120.1 (m).

Provenance & Evidence