Thionyl Chloride → 4,4-Difluorocyclohexane-1-carbonyl chloride
Reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8](O)=[O:9])[CH2:4][CH2:3]1.S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([Cl:14])=[O:9])[CH2:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4,4-Difluorocyclohexanecarboxylic acid (118.2 g, 0.72 mol) was dissolved in toluene (296 ml). To the clear solution was added thionyl chloride (261 ml, 3.6 mol) and the resultant solution was heated under reflux for 1.5 hours. A sample was taken and concentrated and 1H-NMR indicated complete conversion to the title compound. The reaction was cooled to room temperature and the thionyl chloride was removed under reduced pressure and replaced with toluene to give the title compound as a toluene concentrate at a total volume of 591 ml.
Workup
- temperatureunder reflux for 1.5 hours
- concentrationconcentrated
- customthe thionyl chloride was removed under reduced pressure
Sources & evidence
- ORD record
- ord-ee4a44f2ed594671823d17e7904d833e
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06667314B2
Reaction notes
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