N-(4-chloro-2,5-dimethoxyphenyl)-3-fluoro-4-methoxybenzamide → N-(4-Chloro-2,5-dihydroxyphenyl)-3-fluoro-4-hydroxybenzamide

HRID 1007332

반응식

HRID 1007332 반응식
[Cl:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=2)=[C:4]([O:22]C)[CH:3]=1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=2)=[C:4]([OH:22])[CH:3]=1

참가 물질

3

반응물 1

HCID 8409357N-(4-chloro-2,5-dimethoxyphenyl)-3-fluoro-4-methoxybenzamide

생성물 1

HCID 21907381N-(4-Chloro-2,5-dihydroxyphenyl)-3-fluoro-4-hydroxybenzamide수율 91.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Boron trifluoride dimethyl sulfide complex (70 mL) was added into a mixture of N-(4-chloro-2,5-dimethoxyphenyl)-3-fluoro-4-methoxybenzamide (1.75 g, 5.15 mmol) and CH2Cl2 (35 mL). After stirring for 20 h, the solvent and the excess reagent were evaporated under a nitrogen stream in the hood. The residue was taken in a mixture of ice and HCl (1N) and extracted with EtOAc. The organic layer was washed with HCl (1N) and dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc 5/3/2, and AcOH 10 mL per 1 liter of the eluting solvent) gave a white solid (1.4 g, 91% yield, m.p. 254-256° C.); MS m/e 296 (M−H)+.

후처리

  1. customthe solvent and the excess reagent were evaporated under a nitrogen stream in the hood
  2. additionThe residue was taken in a mixture of ice and HCl (1N)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with HCl (1N)
  5. dry with materialdried over MgSO4
  6. customEvaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc 5/3/2, and AcOH 10 mL per 1 liter of the eluting solvent)

출처 및 근거

ORD 기록
ord-106ae1eea1f04c73a79ec916ab2bb3b0
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794403B2

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