Reaktion #7777

Reaktionsgleichung

2-aminophenol

diisopropylethylamine

3-bromo-4-methylbenzoic acid

thionyl chloride

→

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 1 h
2. 2
   SonstigeThe excess thionyl chloride was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in THF (10 mL)
4. 4
   workup.ADDITIONwas added to
5. 5
   Temperatura cooled
6. 6
   SonstigeThe solvent was then removed
7. 7
   Sonstigethe residue was purified by flash chromatography on silica gel eluting with EtOAc:hexane (1:5 to 1:4)

Vorschrift

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.

Quelle