Dimethyl Sulfide → (2,6-Dichloro-5-fluoropyridin-3-yl)methanol

Participants

Reaction Steps

To a stirred mixture of 2,6-dichloro-5-fluoro-nicotinic acid (1.0 g, 4.76 mmol) in dry THF (50 mL) under argon was added neat BH3.DMS (1.35 mL, 14.29 mmol) dropwise. The resulting mixture was heated to reflux for 3 hours, cooled to room temperature and quenched by the dropwise addition of water (4 mL). The reaction mixture was concentrated in vacuo. The crude alcohol was diluted with EtOAc, washed with 1N NaOH, 1N HCl, saturated aqueous NaHCO3 solution and brine. The EtOAc layer was dried (MgSO4), filtered and concentrated in vacuo to give 1A (0.93 g, 97%). HPLC Rt=1.79 min (Column: YMC ODS-A 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA); LCMS Found: (M+H)+=210.

Provenance & Evidence