Thionyl Chloride → 1-Chloro-4-(chloromethyl)-2,5-difluorobenzene
Reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9]O)=[C:4]([F:11])[CH:3]=1.S(Cl)([Cl:14])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([CH2:9][Cl:14])=[CH:6][C:7]=1[F:8]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
Step B A mixture of (4-chloro-2,5-difluoro-phenyl)-methanol (5.5 g, 32 mmol) in thionyl chloride (25 mL) was heated at refluxing (100° C.) for 30 min. The mixture was cooled to room temperature and concentrated. The residue was diluted with ethyl acetate, washed with saturated aqueous NaHCO3 solution, water, brine, dried over MgSO4, and concentrated to give 1-chloro-4-chloromethyl-2,5-difluoro-benzene as a yellow oil (2.1 g, 34%).
Workup
- temperaturewas heated
- temperatureThe mixture was cooled to room temperature
- concentrationconcentrated
- additionThe residue was diluted with ethyl acetate
- washwashed with saturated aqueous NaHCO3 solution, water, brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1890021a17c8485abebe3a6404224499
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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