Chloride → 4-Chlorobenzene-1,2-dicarbonyl dichloride

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To a 1--1 three-necked flask, equipped with a mechanical stirrer, a condenser with a gas outlet and an equa-pressured addition funnel, is charged 241.5 g (1 mole) of 4-chloratetrahydrophthaloyl chloride and 36 g of chlorobenzene. The mixture is heated to 100°-110° C. with stirring. Bromine, 320 g (2 moles) is added dropwise into the solution in a sub-surface manner. The color dissipates quickly and an evolution of gas occurs. When approximately 240 g of bromine has been added, the pot temperature is raised to 135° C. The addition of bromine continues until completion. The pot temperature is then raised to 165°-170° C. for 2-4 fours. During this period, an additional amount of bromine, such as about 10 to 15 g, may be added to complete the conversion of 4-chlorotetrahydrophthaloyl chloride. A good yield of 4-chlorophthaloyl chloride will be obtained from the distillation of the mixture.

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