Water → N-(4-Chlorophenoxyethyl)-3-(2-hydroxyphenyl)propanamide

HRID 350831노트

반응식

HRID 350831 반응식
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:21])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)Cl.O>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:21])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 21055042N-(4-Chlorophenoxyethyl)-3-(2-methoxyphenyl)propanamideHCID 22277759Boron tribromide dichloromethane

생성물 1

HCID 21055041N-(4-Chlorophenoxyethyl)-3-(2-hydroxyphenyl)propanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-(4-Chlorophenoxyethyl)-3-(2-methoxyphenyl)propanamide (12.8 g, 38.3 mmol) was dissolved in methylene chloride (10.0 mL). Subsequently, a 1.0M-boron tribromide/methylene chloride solution (49.8 mL, 49.8 mmol) was slowly added dropwise thereto under ice-cooling, followed by stirring for 1 hour at room temperature. Subsequently, water was slowly added dropwise thereto under ice-cooling, followed by stirring for 30 minutes. The resultant mixture was extracted with chloroform. The organic layer was washed with brine, and the resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by column chromatography (n-hexane/ethyl acetate=20/1), whereby a white solid was obtained (11.6 g, 95%).

후처리

  1. temperatureunder ice-cooling
  2. temperatureunder ice-cooling
  3. stirringby stirring for 30 minutes
  4. extractionThe resultant mixture was extracted with chloroform
  5. washThe organic layer was washed with brine
  6. dry with materialto drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by column chromatography (n-hexane/ethyl acetate=20/1), whereby a white solid
  7. customwas obtained (11.6 g, 95%)

출처 및 근거

ORD 기록
ord-07c1053e9da44d899d3f5ded0ec14faa
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183295B2

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