N-Iodosuccinimide → 2-(4-Fluorobenzyl)-5-iodothiophene

Participants

Reaction Steps

A mixture of 2-(4-fluorophenylmethyl)thiophene (3.85 g, 20.0 mmol), prepared as described in step 1, and N-iodosuccinimide (4.50 g, 20.0 mmol) in 1:1 chloroform-acetic acid (40 mL) was stirred at ambient temperature for 1 hour and then diluted with an equal volume of water. The organic layer was washed with saturated aqueous NaHCO3 solution (2×50 mL), 10% aqueous sodium thiosulfate solution (2×50 mL) and once with brine. After drying over MgSO4, the organic layer was concentrated in vacuo to give 6.07 g (95%) of 2-iodo-5-(4-fluorophenylmethyl)thiophene as a gold colored oil.

Provenance & Evidence