3-Iodo-6-methoxy-2-methylbenzo[b]thiophene → 6-Methoxy-2-methylbenzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

t-BuLi (1.7 M in pentane; 0.32 ml; 0.54 mmol) was added to a solution of the 3-iodo-6-methoxy-2-methylbenzo[b]thiophene (0.0863 g; 0.27 mmol) in anhydrous THF (2.5 ml) at −78° C. under N2. The mixture was allowed to warm up to 0° C. and quenched by the addition of saturated NH4Cl (1 ml). This was diluted to 15 ml with diethyl ether and washed with 5% NaHCO3 (10 ml), dried over anhydrous MgSO4, filtered off and filtrate evaporated to dryness. The residue was purified by flash column chromatography (SiO2, hexane, hexane/ethyl acetate 9.5:0.5) to give the title compound (0.024 g; 50% yield) as colourless solid. 1H-NMR (CDCl3) 2.53 (s, 3H); 3.84 (s, 3H); 6.86 (s, 1H); 6.92 (dd, 1H, J 2.24, 8.87 Hz); 7.222 (d, 1H, J=2.24 Hz); 7.51 (d, 1H, J=8.67 Hz).

Provenance & Evidence