Reacción #1269857

Ecuación de reacción

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

THF

n-BuLi

Br2

→

desired product

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

Disolventes

cyclohexane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added over 10 min
2. 2
   TemperaturaThe reaction mixture was then cooled to 0° C.
3. 3
   Otrocarefully quenched with HCl (1M, 32 mL)
4. 4
   Extracciónextracted with EtOAc (2×)
5. 5
   Lavadophases were washed with aq. sodium thiosulfate (20%)
6. 6
   Secadodried over MgSO4
7. 7
   Otroevaporated to dryness

Procedimiento

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.

Fuente