Sodium Iodide → 5-Iodo-3-methyl-2-(4-propylbenzyl)thiophene

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromo-3-methyl-2-(4-propylbenzyl)thiophene (46, 0.86 g, 2.77 mmol), sodium iodide (0.83 g, 5.53 mmol) and copper(I) iodide (0.053 g, 0.277 mmol) in dioxane (5.2 mL) was added N,N′-dimethylethylenediamine (0.060 mL, 0.553 mmol). The resulting mixture was heated to 110° C. and stirred for 16 hours. After cooling to room temperature, the reaction mixture was filtered through a plug of Celite® and then washed with EtOAc (50 mL). The filtrate was washed with brine and dried over MgSO4. The organic phase was evaporated under vacuum to provide 5-iodo-3-methyl-2-(4-propylbenzyl)thiophene 47 (0.95 g, 2.66 mmol, 96%) as a yellow oil, which was used without further purification.

Provenance & Evidence