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

HRID 858225

反応式

HRID 858225 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5acb907bd7bd40eda99a857aaab1ed4e
出典データセット
uspto-grants-2006_12
特許番号
US07148247B2

関連ノート

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