Thionyl bromide → 4-(Bromomethyl)-3,5-difluoropyridine
Reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:10])[C:7]=1[CH2:8]O.S(Br)([Br:13])=O>C(Cl)Cl.CN(C=O)C>[Br:13][CH2:8][C:7]1[C:2]([F:1])=[CH:3][N:4]=[CH:5][C:6]=1[F:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
(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).