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

HRID 2215176ノート

反応式

HRID 2215176 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-42c7e451eef6492c88e55e65ba0db138
出典データセット
uspto-grants-2006_09
特許番号
US07109226B2

反応ノート

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