Diisobutylaluminumhydride → Benzo[b]thiophene, 7-fluoro-4-methoxy-

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-fluoro-4-methoxy-1-benzothiophen-2(3H)-one (1.06, 5.4 mmol) in dichloromethane (10 mL) at 0° C. was added slowly a solution of diisobutylaluminium hydride in dichloromethane (1 M, 8.04 mL, 8.0 mmol). After 30 mins the reaction was quenched by careful addition of aqueous hydrochloric acid (6 N, 25 mL). The mixture was concentrated to remove the dichloromethane, the aqueous residue was then stirred at 35° C. for 2 h. The aqueous solution was extracted with diethyl ether (3×50 mL), washed with aqueous sodium hydroxide (2 N, 50 mL), brine (50 mL) then dried (MgSO4) and the solvent evaporated in vacuo to give the title compound (0.86 g, 87%) as a purple oil; δH 7.44–7.38 (1H, m, ArH), 7.36–7.24 (1H, m, ArH), 6.88–6.80 (1H, m, ArH), 6.57–6.49 (1H, m, ArH) and 3.82 (3H, s, OCH3).

Provenance & Evidence