Water → 4-Bromo-2-chloro-6-methylbenzoic acid
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[Cl:12]N1C(=O)CCC1=O.O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:9]([Cl:12])[CH:10]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-bromo-2-methyl-benzoic acid (6.45 g, 30 mmol,), N-chlorosuccinimide (4.67 g, 35 mmol), and palladium (II) acetate (0.675 g, 3 mmol) in dry DMF (35 mL) was heated under a nitrogen atmosphere at 100° C. for 36 h. After this time, the reaction mixture was cooled to ambient temperature and poured into water. The aqueous solution was extracted with ethyl acetate (2×100 mL) and the combined organic extracts washed with aqueous sodium thiosulphate (30 mL) and then brine (30 mL). The remaining organic solution was dried over anhydrous MgSO4, filtered, and concentrated to give 4-bromo-2-chloro-6-methyl-benzoic acid. The product was used without further purification.
Workup
- temperatureAfter this time, the reaction mixture was cooled to ambient temperature
- extractionThe aqueous solution was extracted with ethyl acetate (2×100 mL)
- washthe combined organic extracts washed with aqueous sodium thiosulphate (30 mL)
- dry with materialThe remaining organic solution was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-29de73bbdc35461dba6dc6d934cf959e
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968570B2
Reaction notes
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