Réaction #1269857

Équation de réaction

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

THF

n-BuLi

Br2

→

desired product

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

Solvants

cyclohexane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added over 10 min
2. 2
   TempératureThe reaction mixture was then cooled to 0° C.
3. 3
   Autrecarefully quenched with HCl (1M, 32 mL)
4. 4
   Extractionextracted with EtOAc (2×)
5. 5
   Lavagephases were washed with aq. sodium thiosulfate (20%)
6. 6
   Séchagedried over MgSO4
7. 7
   Autreevaporated to dryness

Mode opératoire

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.

Source