C1C=CN=CC=1.[FH:7].[Cl:8][C:9]1[CH2:10][C:11]2[C:16](=[O:17])[O:15][C:13](=[O:14])[C:12]=2[CH2:18][CH:19]=1.[Br:20]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:20][CH:19]1[CH2:18][C:12]2[C:13]([O:15][C:16](=[O:17])[C:11]=2[CH2:10][C:9]1([Cl:8])[F:7])=[O:14]Pyridinium poly(hydrogen fluoride) was added to a solution of 4-chloro-3,6-dihydrophthalic anhydride (6.5 g) in methylene chloride (10.1 g) at room temperature. Bromine (3.1 g) was added. A violent reaction occurs. The solution was allowed to stand for 6 hours and then was poured into a two phase mixture of methylene chloride (30 ml) and solid sodium carbonate. The suspension was stirred for 10 minutes until bubbling stopped. The mixture was filtered and the methylene chloride removed under reduced pressure. The material was purified by a bulb to bulb distillation (140° C. air temperature and 2.8 torr) to give a yellowish solid, (3.74 g).
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