Реакция #1973987

Уравнение реакции

diketene

4-bromo-2-nitroaniline

Triethylamine

→

title compound

Выход 74.0%

N-(4-bromo-2-nitrophenyl)-3-oxobutanamide

Выход 74.0%

Растворители

toluene

toluene

toluene

Условия реакции

Обработка

1. 1
   Температураthe solution was heated
2. 2
   Температураat reflux for 5 h
3. 3
   Температураrefluxing
4. 4
   КонцентрированиеThe cooled solution was concentrated in vacuo
5. 5
   Другоеthe crude product purified by column chromatography on silica gel eluting with 2:1 hexane/EtOAc

Методика

A solution of diketene (0.32 ml, 4.15 mmol) in toluene (2 ml) was added to an 80° C. solution of 4-bromo-2-nitroaniline (900 mg, 4.15 mmol) in toluene (7 ml) and the solution was heated at reflux for 5 h. Triethylamine (0.58 ml, 4.15 mmol) in toluene (2 ml) was added and refluxing was continued for 30 min. The cooled solution was concentrated in vacuo and the crude product purified by column chromatography on silica gel eluting with 2:1 hexane/EtOAc to give the title compound as a yellow solid (920 mg, 74%).

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