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

HRID 2215176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215176
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-42c7e451eef6492c88e55e65ba0db138
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109226B2

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