Hydrochloric Acid → HCID 67117368, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromo-5-fluoroanisole (11.8 g, 57.6 mmol) in tetrahydrofuran (60 ml) was dropped into the magnesium (1.40 g, 57.6 mmol) in refluxed tetrahydrofuran (32 ml) containing small amount of 1,2-dibromoethane and refluxed for 15 min. After addition of tetrahydrofuran (50 ml), the solution was cooled to −78° C. and diethyl oxalate (7.41 g; 50.7 mmol) in diethyl ether (50 ml) was dropped into the solution. After stirring at the same temperature for 30 min, the solution was warmed to −10° C. and 1N aqueous hydrogen chloride (50 ml) and water were added. Organic layer was extracted with diethyl ether, washed with brine and dried over magnesium sulfate. After removal of the solvent under reduced pressure, purification of the residue by silica gel column chromatography (eluent: hexane/ethyl acetate=5/2) gave ethyl 2-(4-fluoro-2-methoxyphenyl)-2-oxoacetate (6.80 g, 59%)

Provenance & Evidence