Aluminum(III) Chloride → 7-Chloro-6-fluoroisoquinoline

Participants

Reaction Steps

343.6 (2.54 mol) of AlCl3 were suspended in 1.1 l of dichloromethane and were stirred for 30 min with a mechanical stirrer. To this suspension, a solution of 204 g (0.51 mol) (N-(3-Chloro-4-fluoro-benzyl)-N-(2,2-dimethoxy-ethyl)-4-methyl-benzene-sulfonamide (2) was added and the mixture was stirred at room temperature for 5 h. After standing overnight, the reaction suspension was poured on ice, the organic layer was separated and the aqueous phase was extracted twice with dichloromethane. The combined organic layers were washed twice with 1 N NaOH and saturated NaHCO3-solution, dried with MgSO4 and evaporated. The obtained crude product was purified by silicagel chromatography (heptane/ethyl acetate 1:1), which gave 61.3 g of the title compound. Rt=0.73 min (Method B). Detected mass: 182.1 (M+H+).

Provenance & Evidence