Benzyl Chloride → 1-Benzyl-4-trifluoromethylpyridinium chloride
Reaction equation
[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([F:18])([F:17])[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1.CC(OC)(C)C>C(#N)C>[Cl-:8].[CH2:1]([N+:14]1[CH:15]=[CH:16][C:11]([C:10]([F:18])([F:17])[F:9])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of 7.59 mL (65.94 mmol) benzyl chloride in 10 mL of acetonitrile was added to a solution of 10.00 g (65.94 mmol) of 4-trifluoromethylpyridine in 40 mL of acetonitrile and the mixture was stirred for 2 hours at 80° C. Another 1.5 mL of benzyl chloride was added and the mixture was stirred for 22 hours at 80° C. The reaction mixture was cooled to RT and combined with MTBE. The precipitate was filtered off, washed with MTBE, dried in vacuo, and stored in the desiccator. Yield: 14.48 g (80% of theoretical); C13H11F3N.Cl (M=273.681); calc.: molpeak (M+H)+: 238; found: molpeak (M+H)+: 238.
Workup
- stirringthe mixture was stirred for 22 hours at 80° C
- temperatureThe reaction mixture was cooled to RT
- filtrationThe precipitate was filtered off
- washwashed with MTBE
- customdried in vacuo
Sources & evidence
- ORD record
- ord-f383018f8ae34484bddd97f760da5836
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592358B2
Reaction notes
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