Dichloromethane → 3-(Bromomethyl)-2,6-dichloro-5-fluoropyridine

Participants

Reaction Steps

To a stirred mixture of alcohol 1A (3.52 g, 17.9 mmol) in CHCl3 (100 mL) under argon was added 1M PBr3 in CH2Cl2 (18.0 mL, 18.0 mmol). The reaction mixture was heated to reflux for 15 minutes, cooled to room temperature, then poured into a mixture of ice and saturated NaHCO3 solution (200 mL). The pH was adjusted to basic by addition of solid NaHCO3. The aqueous layer was extracted with EtOAc. The combined EtOAc extracts were washed with brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 1B (4.11 g, 88%). HPLC Rt=2.78 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).

Provenance & Evidence