تفاعل #1269857

معادلة التفاعل

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

THF

n-BuLi

Br2

→

desired product

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

المذيبات

cyclohexane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added over 10 min
2. 2
   درجة الحرارةThe reaction mixture was then cooled to 0° C.
3. 3
   أخرىcarefully quenched with HCl (1M, 32 mL)
4. 4
   استخلاصextracted with EtOAc (2×)
5. 5
   غسيلphases were washed with aq. sodium thiosulfate (20%)
6. 6
   تجفيفdried over MgSO4
7. 7
   أخرىevaporated to dryness

الإجراء التجريبي

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.

المصدر