Thionyl Chloride → 2-(4-Chlorophenyl)ethyl chloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.CN(C)C(=O)C.S(Cl)([Cl:19])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][Cl:19])=[CH:4][CH:3]=1Participants
4
Conditions
- Temperature
- 57.5 °C
Procedure
Into a 250-mL round-bottom flask equipped with magnetic stirring, a thermocouple, a condenser, and a nitrogen bubbler vented to caustic scrubber, was charged 2-(4-chlorophenyl)ethanol (25.145 g, 161 mmol) and N,N-dimethylacetamide (0.752 mL, 8.03 mmol). The mixture was heated to 55 to 60° C. and then thionyl chloride (12.30 mL, 169 mmol) was added over 1 h at <62° C. The reaction mixture was stirred at 58 to 62° C. for 2 h and then allowed to cool to <30° C. to give the title compound as a dark brown solution (29.730 g) containing N,N-dimethylacetamide and thionyl chloride. This was transferred to an addition funnel using toluene (5 mL).
Workup
- customInto a 250-mL round-bottom flask equipped with magnetic stirring
- temperatureto cool to <30° C.
Sources & evidence
- ORD record
- ord-e0dc5e84e72840a99f0996ae392558ff
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952197B2
Reaction notes
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