Methanol → Methyl [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetate

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:11][CH2:10]1.S(=O)(=O)(O)O.[CH3:21]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([O:15][CH3:21])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 59570913[3-Bromo-4-(cyclopropylsulfanyl)phenyl]acetic acid

Product 1

HCID 59571017Methyl [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetate

Procedure

A mixture of [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetic acid (13.5 g), concentrated sulfuric acid (0.135 mL), and methanol (40 mL) was stirred under heating and reflux for 4 hours. After leaving to be cooled at room temperature, the solvent was evaporated under reduced pressure, and then a 1 M aqueous sodium hydroxide solution (100 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (100 mL×3). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure to obtain methyl [3-bromo-4-(cyclopropylsulfanyl)phenyl]acetate (13.8 g) as a colorless solid.