1,2-Dichloroethane → 2,3-Dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile

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Reaction Conditions

Reaction Steps

Sulfuryl chloride (3.0 mL, 37.0 mmol) was added to a solution of 4-fluorobenzo[b]thiophene-7-carbonitrile (1.05 g, 5.93 mmol) in 1,2-dichloroethane (30 mL) at room temperature. The mixture was heated at 60° C. for 24 h and then the solvent was removed and the residue mixed with saturated aq. NaHCO3 solution and extracted with 10% EtOAc in hexanes. These extracts were then washed with saturated aq. NaHCO3 solution, water, brine and dried over Na2SO4. Concentration gave the crude 2,3-dichloro-4-fluoro-2,3-dihydrobenzo[b]thiophene-7-carbonitrile as a brown solid (1.57 g). 1H NMR (400 MHz, CDCl3, δ in ppm) 7.68 (dd, J=4.7, 8.6 Hz, 1H), 7.03 (t, J=8.2 Hz, 1H), 5.82 (s, 1H), 5.74 (s, 1H).

Provenance & Evidence