Sodium Iodide → 3-Iodobenzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. Racemic 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 (hexane) to provide 3-iodobenzo[b]thiophene (243 mg, 93% yield) as a pale yellow liquid. 1H NMR (400 MHz, CDCl3): δ 7.88 (d, J=8.0 Hz, 1H), 7.80 (d, J=7.9 Hz, 1H), 7.64 (s, 1H), 7.53-7.40 (m, 2H). 13C NMR (100 MHz, CDCl3): δ 140.2, 138.3, 129.1, 125.22, 125.16, 122.4, 78.2. IR (neat, cm−1): 1416, 1305, 1251, 749, 723. Anal. Calcd. for C8H5IS: C, 36.94; H, 1.94. Found: C, 37.14; H, 1.98.

Provenance & Evidence