Methanol → 2-Fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid methyl ester

반응식

[F:1][C:2]1[C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:30]O>>[CH3:30][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:2]=1[F:1]

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 57963295HCID 57963295, 화합물

생성물 1

HCID 579633152-Fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid methyl ester수율 81%

실험 절차

To 2-fluoro-3-(4-trifluoromethyl-benzenesulfonylamino)-benzoic acid (31, 4.0 g, 11 mmol) in 40 mL of methanol, sulfuric acid (8.8 mL, 0.16 mol) was added and the reaction mixture was refluxed overnight. The resulting reaction mixture was concentrated under vacuum, and the residue was combined with 5% aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (32, 3.35 g, 81%). MS(ESI) [M−H+]−=376.4.