Thionyl Chloride → 5-Bromo-2-fluorobenzoyl chloride
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].O=S(Cl)[Cl:14]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]Participants
3
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 5-bromo-2-fluorobenzoic acid (1.1 g, 5.2 mmol) in SOCl2 (11.8 g, 99 mmol) was warmed to 90° C. and was stirred for 2 h. The mixture was cooled to ambient temperature and was concentrated under reduced pressure. The residue was diluted with toluene (5 mL) and was concentrated under reduced pressure. This dilution with toluene and concentration was repeated two additional times to remove excess SOCl2. The crude acid chloride was carried on without purification or characterization.
Workup
- temperatureThe mixture was cooled to ambient temperature
- concentrationwas concentrated under reduced pressure
- additionThe residue was diluted with toluene (5 mL)
- concentrationwas concentrated under reduced pressure
- concentrationThis dilution with toluene and concentration
- customto remove excess SOCl2
- customThe crude acid chloride was carried on without purification or characterization
Sources & evidence
- ORD record
- ord-73f9bb948b0944feb0c5ffcb567edbe3
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895592B2
Reaction notes
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