Oxalyl chloride → HCID 58385804, compound

Participants

Reaction Steps

Oxalyl chloride (9.5 mL) is added to a solution of 2-bromo-5-iodo-benzoic acid (25.0 g) in dichloromethane (50 mL). A few drops of DMF are added and the mixture is stirred at room temperature overnight. Then, the reaction solution is concentrated under reduced pressure and the residue is taken up in dichloromethane (50 mL) and ethylbenzene (23 mL). The resulting solution is cooled in an ice-bath and aluminum trichloride (12.5 g) is added in portions. Then, the cooling bath is removed and the reaction mixture is stirred at room temperature for 4 h. After consumption of the intermediate substituted benzoyl chloride, the reaction mixture is poured onto crushed ice and the organic phase is separated off. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed in succession with 1 M hydrochloric acid, 1 M potassium hydroxide solution and brine. The organic phase is dried (sodium sulphate) and the solvent is removed under reduced pressure to give the product as an oil that crystallizes on standing.

Provenance & Evidence