Thionyl Chloride → 5-Bromo-2-chlorobenzoyl chloride
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1.CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([Cl:14])=[O:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 5-bromo-2-chloro-benzoic acid 15a (7.24 g, 30.8 mmol) in toluene (100 mL) were added thionyl chloride (3.6 mL, 49.2 mmol) and N,N-dimethylformamide (0.2 mL, 2.6 mmol) in turn at 0° C. The mixture was warmed up to 100° C. and stirred for 4 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give the title compound 21d as yellow oil (7.82 g, 100%). This material was not further purified.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3f88896c5fef4ec4b78f4cefb8b45c29
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394329B2
Reaction notes
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