Dichloromethane → N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4, 5-dihydroxyphenyl) propenamide

반응식

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

참가 물질

반응물 3

HCID 6344Dichloromethane

HCID 25134Boron tribromide

HCID 54180841N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide

생성물 1

HCID 53807593N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4, 5-dihydroxyphenyl) propenamide수율 35.4%

실험 절차

Demethylation was effected in the same as in Example 2 with N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4-hydroxy-5-methoxyphenyl) propenamide (470 mg, 1.36 mmol) and 1M solution of boron tribromide in methylene chloride (3.50 ml, 34.50 mmol). The resulting solid was recrystallized from ethanol-water to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-fluoro-4, 5-dihydroxyphenyl) propenamide (160 mg, 35% in yield) as yellow powder.