Oxalyl chloride → HCID 15628583, compound

Participants

Reaction Steps

A mixture of 2-[2-(4-fluorophenyl)ethyl]-5-fluorobenzoic acid (2.02 g, 7.71 mmol, 1 equiv) and oxalyl chloride (1.37 g, 10.8 mmol, 1.4 equiv) in CH2Cl2 (20 mL) was refluxed for 30 min. The resulting solution was then added to a stirring suspension of aluminum chloride (1.44 g, 10.8 mmol, 1.4 equiv) in CH2Cl2 (50 mL). This mixture was refluxed for 1 h. The reaction mixture was then washed with 1N HCl (3×20 mL), aq. satd. NaCl (1×50 mL), and H2O (1×50 mL). The organic layer was dried (anhyd. Na2SO4) and rotary evaporated to provide 1.6 g of a light-orange-colored semisolid. This material was chromatographed (3:1 hexane/CHCl3) through silica gel (150 mm×25 mm dia.). Evaporation of the combined fractions containing product provided 0.93 g (49%) of the desired product as a light-yellow shiny solid.

Provenance & Evidence