N-bromobutanimide → 3-bromo-5-fluoro-2-methylbenzoic acid
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[Br:12]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:12][C:4]1[C:5]([CH3:11])=[C:6]([CH:10]=[C:2]([F:1])[CH:3]=1)[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of 5-fluoro-2-methyl-benzoic acid (20 g, 130 mmol) in conc. sulfuric acid (200 mL) was added N-bromosuccinimide (24.3 g, 136 mmol) portionwise. The resulting mixture was stirred at 0° C. for 3 hrs, then warmed to room temperature and stirred for 16 hrs. Then the mixture was poured slowly into ice water (2 L), and extracted with EtOAc. The combined organic layers were washed with water and brine, dried and concentrated to provide 3-bromo-5-fluoro-2-methyl-benzoic acid, which was used directly in the next step.
Workup
- temperaturewarmed to room temperature
- stirringstirred for 16 hrs
- extractionextracted with EtOAc
- washThe combined organic layers were washed with water and brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a6c6c9106d84460a807180d1309caa0a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673920B2
Reaction notes
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