Thionyl bromide → 4-(Bromomethyl)-3,5-difluoropyridine

Participants

Reaction Steps

(3,5-Difluoro-4-pyridyl)methanol (6.11 g, 42.11 mmol) was dissolved in CH2Cl2 (140 mL). At 0° C. Thionyl bromide (3.589 mL, 46.32 mmol) was added slowly, then 1 drop of DMF was added: the solution turned yellow with gas evolution. The reaction mixture was stirred at rt for 1.5 h. It was quenched with 10 ml water. The pH was made basic (pH=9) with aq NaHCO3. The water layer was extracted 3 times with CH2Cl2. The combined organic layers were washed with brine. The organic phase was dried with Na2SO4, filtrated and the filtrate evaporated. The desired product was obtained as a brown liquid (9.68 g, lacrimator).

Provenance & Evidence