Sodium Iodide → 3-Iodobenzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %), 3-bromobenzo[b]thiophene (131 μL, 1.00 mmol), m-xylene (0.80 mL), and diglyme (0.20 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 130° C. for 22 h. The resulting suspension was allowed to reach room temperature, diluted with hexane (10 mL), and filtered through silica gel (2×2 cm) eluting with hexane (50 mL). The filtrate was concentrated, and the residue was purified by flash chromatography on silica gel to provide 3-iodobenzo[b]thiophene (243 mg, 93% yield) as a pale yellow liquid.

Provenance & Evidence