反应详情

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 in vacuo, the residue was dissolved in THF (10 mL), and was added to a cooled (0° C.) mixture of 2-aminophenol (510 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:hexane (1:5 to 1:4) to afford 3-bromo-N-(2-hydroxyphenyl)-4-methylbenzamide.

1. temperaturewas refluxed for 1 h
2. customThe excess thionyl chloride was removed in vacuo
3. dissolutionthe residue was dissolved in THF (10 mL)
4. additionwas added to
5. temperaturea cooled
6. customThe solvent was then removed
7. customthe residue was purified by flash chromatography on silica gel eluting with EtOAc:hexane (1:5 to 1:4)