Methanol → Methyl 3-bromo-2-methoxybenzoate
Reaction equation
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:13]O>S(=O)(=O)(O)O>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[C:3]=1[O:11][CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Approximately two drops of sulfuric acid were added to a solution of 3-bromo-2-methoxy-benzoic acid (10.00 g, 43.30 mmol) in methanol and the resulting reaction mixture was refluxed for 14 hours. The reaction mixture was cooled to room temperature, and concentrated, then diluted with EtOAc. The organic layer was washed with saturated NaHCO3 (3×150 mL), H2O (2×250 mL), brine (1×250 mL) and dried over MgSO4. The crude product was purified by column chromatography using hex:EtOAc (4.5:0.5) as the eluant to give the title ester. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 3.91 (s, 3H), 3.94 (s, 3H), 6.92 (d, J=8.79 Hz, 1H), 7.99 (dd, J=8.79 Hz, 1H), 8.24 (d, J=2.35 Hz, 1H).