The chlorination of isophthaloyl and terephthaloyl chloride in the presence of iron leads to 5chloroisophthaloyl chloride and 2,3,5,6-tetrachloroterephthaloyl chloride, respectively. The latter compound, due to its highly hindered structure, shows considerable stability toward reagents which are capable of attacking an acid chloride. The chlorinated phthaloyl chlorides have been converted to a number of derivatives.Experimental 5-Chloroisophthaloyl Chloride.-A mixture of 144 g. of isophthaloyl chloride and 5 g. of iron filings was treated with chlorine at 95-100°until there was no further increase in weight. The reaction mixture was diluted with carbon tetrachloride and filtered. The filtrate was concentrated and distilled in vacuo.
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