Methanol → Methyl 2-(4-bromophenyl)acetate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1Participants
4
Procedure
(4-Bromo-phenyl)-acetic acid (60 g) was dissolved in methanol (200 mL). Concentrated sulfuric acid (1 mL) was added and the reaction mixture heated to reflux on an oil bath for 1.5 h. The reaction mixture was allowed to cool and concentrated in vacuo. The concentrate was diluted with diethyl ether (400 mL) and washed with brine (5×4 mL). The remaining organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness in vacuo to yield the title compound (62 g).
Workup
- temperaturethe reaction mixture heated
- temperatureto reflux on an oil bath for 1.5 h
- temperatureto cool
- concentrationconcentrated in vacuo
- additionThe concentrate was diluted with diethyl ether (400 mL)
- washwashed with brine (5×4 mL)
- dry with materialThe remaining organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to dryness in vacuo
Sources & evidence
- ORD record
- ord-e55c7dc353694b358409de80dba11b4e
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07250518B2
Reaction notes
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