Water → Methyl 4-[(acetyloxy)methyl]-3-bromobenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12]Br)[C:5]([O:7][CH3:8])=[O:6].[C:14]([O-:17])(=[O:16])[CH3:15].[K+].O.C(OCC)(=O)C>CN(C)C=O>[C:14]([O:17][CH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Br:1])(=[O:16])[CH3:15]Participants
Procedure
10.85 g of methyl 3-bromo-4-(bromomethyl)benzoate was dissolved in 108 mL of N,N-dimethylformamide, to which 3.46 g of potassium acetate was added at room temperature, and this solution was stirred for 17.5 hours at the same temperature. The reaction mixture was added to a mixture of water and ethyl acetate, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to yield 6.43 g of methyl 4-[(acetyloxy)methyl]-3-bromobenzoate as white solid.
Workup
- additionwas added at room temperature
- customthe organic phase was separated
- washAfter the resultant organic phase was washed with water
- dry with materiala saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled out under reduced pressure
- customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1]
Sources & evidence
- ORD record
- ord-a46ea5b9693d4b6d9bc0919224967d5e
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772285B2
Reaction notes
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