Triethylsilane → 4-Fluoro-7-methoxy-2,3-dihydrobenzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-7-methoxy-1-benzothiophene (1.55 g, 8.5 mmol, 1 eq) in trifluoroacetic acid (40 ml) was added triethylsilane (3.40 ml, 21.25 mmol, 2.5 eq). The mixture was heated to 60° C. for 48 hours, then cooled to room temperature and the solvent removed in vacuo. The crude product was purified by flash chromatography with a gradient of 40-60% chloroform in heptane to give 1.24 g, 80% recovered starting material and 199 mg, 13% yield of the title compound as a colourless oil: δH (300 MHz, CDCl3) 3.78-6.58 (2H, m, ArH), 3.82 (3H, s, CH3) and 3.44-3.30 (4H, m, SCH2CH2).

Provenance & Evidence