Thionyl Chloride → 4-Chloromethyl-3-Fluoro-Pyridine Hydrochloride
Reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.S(Cl)([Cl:12])=O>C(#N)C>[ClH:12].[Cl:12][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
6.710 g (52.785 mmol) of (3-fluoropyridin-4-yl)methanol was put in 29 ml acetonitrile and heated to 50° C. Then a solution of 7.701 ml thionyl chloride in 14.5 ml acetonitrile was added dropwise and the reaction mixture was stirred for 4 h at 50° C. Then the reaction mixture was concentrated by evaporation and was co-distilled three times with dichloromethane. After drying under high vacuum, 10.27 g of the title compound was obtained, which was used in the next step without further purification.
Workup
- concentrationThen the reaction mixture was concentrated by evaporation
- customAfter drying under high vacuum
Sources & evidence
- ORD record
- ord-53cd80e5e96045c68d55a431d243c5a9
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859569B2
Reaction notes
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