Reaktion #7784

Reaktionsgleichung

3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide

p-toluenesulfonic acid

→

2-(3-bromo-4-methylphenyl)-1,3-benzoxazole

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 4 h
2. 2
   Filtrationfiltered through a Celite pad
3. 3
   SonstigeThe filtrate was evaporated to dryness
4. 4
   Sonstigethe residue was purified by flash chromatography on silica gel using a gradient of EtOAc

Vorschrift

A mixture of 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide (554 mg, 1.8 mmol), p-toluenesulfonic acid (2.41 g, 12.7 mmol) and toluene (50 mL) was refluxed for 4 h, cooled to rt, and filtered through a Celite pad. The filtrate was evaporated to dryness and the residue was purified by flash chromatography on silica gel using a gradient of EtOAc:hexanes (0 to 30 min:0 to 15% EtOAc) to afford 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole as a colorless solid. MS (ESI) 288 (M+).

Quelle