Thionyl Chloride → 4-Chloro-2-(trifluoromethyl)pyridine
Reaction equation
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.S(Cl)([Cl:14])=O>ClC1C=CC=CC=1Cl.CN(C=O)C>[Cl:14][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
4-Hydroxy-2-trifluoromethylpyridine (6.4 g, 39 mmol) was dissolved in 1,2-dichlorobenzene (64 g). Thionylchloride (23.2 g, 195 mmol) and DMF (10 drops) were added to the reaction mixture which was then heated to 70 to 80° C. After about 2 hours the reaction was completed and excess thionyl chloride was removed at an elevated temperature. The desired product was distilled under reduced pressure (50° C., 15 mbar) to yield 4-chloro-2-trifluoromethyl-pyridine (6.5 g, 36 mmol, yield: 92%). If required, remaining DMF was removed using an aqueous work-up.
Workup
- customexcess thionyl chloride was removed at an elevated temperature
- distillationThe desired product was distilled under reduced pressure (50° C., 15 mbar)
Sources & evidence
- ORD record
- ord-2855637214094713b6aecb3c5b2cc13d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716487B2
Reaction notes
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