Acetic Acid → 2-(4-Fluorobenzyl)-5-iodothiophene

Temperature

40 °C

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.

1. customwas consumed by GC analysis
2. temperatureThe reaction mixture was cooled to ambient temperature
3. additionH2O (150 mL) and isopropyl acetate (150 mL) were added
4. customThe aqueous layer was separated
5. extractionextracted with isopropyl acetate (100 mL)
6. washwashed with H2O (100 mL), saturated aqueous NaHCO3 (2×100 mL), and saturated aqueous Na2S2O3 (2×100 mL)
7. additionThe organic phase was then treated with activated carbon
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-7f84d861125a4168a69398dc60f21f2d

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05616596