Chlorobenzene → methyl 7-chloronaphthalene-1-carboxylate

Participants

Reaction Steps

A mixture of 50 ml of methyl 2-furoate and 400 ml of chlorobenzene is stirred at 0° for 30 minutes, at RT for 1.5 hours and at 100° for 16 hours. 121 g of anhydrous AlCl3 are added by portion at 0°. The solution obtained is cooled, poured in an ice-bath and stirred for 30 minutes before extraction of the aq. phase with ether. The organic phase obtained is washed with aq. 10% NaHCO3 solution and brine, dried and solvent is evaporated. The residue obtained is purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 99/1 to 95/5) to obtain the title compound.

Provenance & Evidence