Water → 2-(2-Hydroxyphenyl)acetamide

2-Methoxyphenyl acetamide (13.0 g, 78.6 mmol) was dissolved in methylene chloride (10.0 mL). Subsequently, 1.0M boron tribromide in methylene chloride solution (157 mL, 157 mmol) was slowly added dropwise under ice-cooling, and the mixture was stirred for one hour at room temperature. Subsequently, water was slowly added thereto under ice-cooling, and the mixture was stirred for 30 minutes. The mixture was extracted with chloroform, followed by washing the organic layer with brine, drying over anhydrous sodium sulfate. The reaction mixture was subjected to concentration under reduced pressure and purification by column chromatography (n-hexane/ethyl acetate=20/1), whereby a white solid was obtained (1.8 g, 11.9 mmol, 15%).

1. temperaturecooling
2. temperatureunder ice-cooling
3. stirringthe mixture was stirred for 30 minutes
4. extractionThe mixture was extracted with chloroform
5. washby washing the organic layer with brine
6. dry with materialdrying over anhydrous sodium sulfate
7. concentrationThe reaction mixture was subjected to concentration under reduced pressure and purification by column chromatography (n-hexane/ethyl acetate=20/1), whereby a white solid
8. customwas obtained (1.8 g, 11.9 mmol, 15%)

ORD record

ord-b753f151cbe1496ea7e4bc6b37462f55

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109226B2