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

HRID 350831Notes

Reaction equation

HRID 350831 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-07c1053e9da44d899d3f5ded0ec14faa
Source dataset
uspto-grants-2007_02
Patent number
US07183295B2

Reaction notes

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