Реакция #1269857

Уравнение реакции

2-phenyl-1,3-thiazole-4-carboxylic acid

THF

n-BuLi

Br2

→

desired product

5-Bromo-2-phenyl-thiazole-4-carboxylic acid

Растворители

cyclohexane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added over 10 min
2. 2
   ТемператураThe reaction mixture was then cooled to 0° C.
3. 3
   Другоеcarefully quenched with HCl (1M, 32 mL)
4. 4
   Экстракцияextracted with EtOAc (2×)
5. 5
   Промывкаphases were washed with aq. sodium thiosulfate (20%)
6. 6
   Сушкаdried over MgSO4
7. 7
   Другоеevaporated to dryness

Методика

To a solution of 2-phenyl-1,3-thiazole-4-carboxylic acid (3.2 g) in abs. THF (190 mL) was added at 78° C. over 10 min n-BuLi (25 mL, 1.6M in hexanes). After addition, Br2 (1.3 mL) in cyclohexane (7.4 mL) was added over 10 min. The reaction mixture was allowed to warm up to RT and was stirred at this temperature for 3 h. The reaction mixture was then cooled to 0° C., carefully quenched with HCl (1M, 32 mL) and extracted with EtOAc (2×). The combined org. phases were washed with aq. sodium thiosulfate (20%), dried over MgSO4 and evaporated to dryness to give 4.5 g of the desired product. The crude was used without further purification.

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