Methanol → Benzoic acid, 4-fluoro-2-mercapto-, methyl ester

반응식

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([SH:11])[CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([SH:11])[CH:3]=1

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 127373274-Fluoro-2-sulfanylbenzoic acid

생성물 1

HCID 12737328Benzoic acid, 4-fluoro-2-mercapto-, methyl ester수율 70%

실험 절차

A mixture of 4-fluoro-2-sulfanylbenzoic acid (6.0 g, 34.9 mmol), concentrated sulfuric acid (6 mL) in methanol (200 mL) was refluxed for 18 hours under argon atmosphere. The resulting mixture was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water, basified with a saturated aqueous solution of sodium bicarbonate to about pH 8. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 4.54 g of the crude product as a brown oil (yield was 70%), which was used directly for the next step without further purification. MS obsd. (ESI−) [(M−H)−] 185.