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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence