Methanol → Methyl 3-bromo-4-chlorobenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].[CH3:12]O.S(=O)(=O)(O)O>O>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Br:1])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a round bottom flask containing 3-bromo-4-chlorobenzoic acid (5.0 g, 21.2 mmol) (commercially available from Aldrich, CAS No. 42860-10-6) was added a cold solution of MeOH (60 mL) and sulfuric acid (1.4 mL). The mixture was heated to 80° C. and monitored with TLC. After 17 hours, the reaction was cooled to room temperature and diluted with water. The aqueous phase was extracted with diethyl ether (3×50 mL), and the combined organic layers were dried over anhydrous magnesium sulfate. After filtration, the organic solvent was removed in vacuo to yield white solid 13.1 (5.0 g, 96% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.28 (1H, d, J=2.0 Hz), 7.93 (1H, m), 7.52 (1H, d, J=8.2 Hz), 3.93 (3H, s).
Workup
- temperaturethe reaction was cooled to room temperature
- extractionThe aqueous phase was extracted with diethyl ether (3×50 mL)
- dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
- filtrationAfter filtration
- customthe organic solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-57328e8d71cb481bbedfcb6432d245d9
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572934B2
Reaction notes
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