반응 #80453

반응 방정식

2-(4-fluorophenylmethyl)thiophene

I2

acetic acid

sulfuric acid

→

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

용매

isopropyl acetate

H2O

반응 조건

후처리

1. 1
   기타was consumed by GC analysis
2. 2
   온도The reaction mixture was cooled to ambient temperature
3. 3
   workup.ADDITIONH2O (150 mL) and isopropyl acetate (150 mL) were added
4. 4
   기타The aqueous layer was separated
5. 5
   추출extracted with isopropyl acetate (100 mL)
6. 6
   세척washed 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
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo

실험 절차

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.

출처