Реакция #161475

Уравнение реакции

p-toluenesulfonic acid monohydrate

2-Chloro-4-fluoro-5-nitrobenzoic acid

2-aminophenol

WSC

→

title compound

Выход 26.3%

2-(4-chloro-2-fluoronitrobenzen-5-yl)benzoxazole

Выход 26.3%

Растворители

Water

CHCl3

Условия реакции

Обработка

1. 1
   Экстракцияthis was extracted with chloroform/acetone (3:1)
2. 2
   ДругоеAfter the organic layer obtained
3. 3
   Сушкаwas dried over anhydrous sodium sulfate, it
4. 4
   Фильтрацияwas filtered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеTo a toluene (80 mL) solution of the solid obtained
7. 7
   Температураthis was heated
8. 8
   Температураto reflux for 40 hours
9. 9
   КонцентрированиеAfter the reaction solution was concentrated
10. 10
    workup.ADDITIONwater was added
11. 11
    Фильтрацияthe precipitated crystals were filtered
12. 12
    Промывкаafter being washed with water
13. 13
    Другоеwere dried

Методика

2-Chloro-4-fluoro-5-nitrobenzoic acid (4.00 g, 18.2 mmol), 2-aminophenol (2.09 g, 20.1 mmol), CHCl3 (80 mL), and WSC (3.84 g, 20.0 mmol) were added together and stirred at room temperature for 2 hours. Water was added, and this was extracted with chloroform/acetone (3:1). After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. To a toluene (80 mL) solution of the solid obtained was added p-toluenesulfonic acid monohydrate (0.18 g, 1.8 mmol), and this was heated to reflux for 40 hours. After the reaction solution was concentrated, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (1.40 g, 26% yield) as yellowish-brown crystals.

Источник