反应 #80453

反应方程式

2-(4-fluorophenylmethyl)thiophene

I2

acetic acid

sulfuric acid

→

2-iodo-5-(4-fluorophenylmethyl)thiophene

溶剂

isopropyl acetate

H2O

反应条件

后处理

1. 1
   其他was consumed by GC analysis
2. 2
   温度The reaction mixture was cooled to ambient temperature
3. 3
   workup.ADDITIONH2O (150 mL) and isopropyl acetate (150 mL) were added
4. 4
   其他The aqueous layer was separated
5. 5
   萃取extracted with isopropyl acetate (100 mL)
6. 6
   洗涤washed with H2O (100 mL), saturated aqueous NaHCO3 (2×100 mL), and saturated aqueous Na2S2O3 (2×100 mL)
7. 7
   workup.ADDITIONThe organic phase was then treated with activated carbon
8. 8
   干燥dried over MgSO4
9. 9
   过滤filtered
10. 10
    浓缩concentrated in vacuo

实验过程

A mixture of 2-(4-fluorophenylmethyl)thiophene (15 g, 78 mmol), prepared as in step 1, HIO3 (2.8 g, 16 mmol), I2 (7.9 g, 1.2 mmol), acetic acid (36 mL), concentrated sulfuric acid (1.2 mL), and H2O (9 mL) was heated at 40° C. for 2 hours at which point all starting material was consumed by GC analysis. The reaction mixture was cooled to ambient temperature and H2O (150 mL) and isopropyl acetate (150 mL) were added. The aqueous layer was separated, neutralized with saturated aqueous K2CO3, and extracted with isopropyl acetate (100 mL). The organic layers were combined and washed with H2O (100 mL), saturated aqueous NaHCO3 (2×100 mL), and saturated aqueous Na2S2O3 (2×100 mL). The organic phase was then treated with activated carbon, dried over MgSO4, filtered, and concentrated in vacuo to give a quantitative yield of 2-iodo-5-(4-fluorophenylmethyl)thiophene as a solution in isopropyl acetate, which is used without further purification.

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