Reacción #7783

Ecuación de reacción

2-aminophenol

diisopropylethylamine

3-bromo-4-methylbenzoic acid

thionyl chloride

→

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 1 h
2. 2
   OtroThe excess thionyl chloride was removed int vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in THF (10 mL)
4. 4
   workup.ADDITIONit was added to
5. 5
   Temperaturaa cooled
6. 6
   OtroThe solvent was then removed
7. 7
   Otrothe residue was purified by flash chromatography on silica gel eluting with EtOAc:hexanes (1:5 to 1:4)

Procedimiento

A mixture of 3-bromo-4-methylbenzoic acid (1.0 g, 4.7 mmol) and thionyl chloride (18 mL) was refluxed for 1 h and then cooled to rt. The excess thionyl chloride was removed int vacuo, the residue was dissolved in THF (10 mL), and it was added to a cooled (0° C.) mixture of 2-aminophenol (507 mg, 4.7 mmol) and diisopropylethylamine (0.90 mL; 5.1 mmol) in THF (18 mL). The resulting mixture was stirred at rt for 4 h. The solvent was then removed and the residue was purified by flash chromatography on silica gel eluting with EtOAc:hexanes (1:5 to 1:4) to afford 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide.

Fuente