[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[C:11]=2[Cl:18])=[N:2]1.Br[CH2:20][C:21]([O:23]CC)=[O:22].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+].[Na]>CN(C)C=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:20][C:21]([OH:23])=[O:22])=[C:12]([Cl:17])[C:11]=2[Cl:18])=[N:2]1The phenol product was warmed at 50° for 30 minutes in 100 ml of dimethylformamide containing 2.90 ml of ethyl bromoacetate and 5.5 g of K2CO3. Twenty mililiters (20 ml) of 20% aqueous NaOH was then added to the mixture and warming was continued an additional 30 minutes with vigorous stirring. The product acid which was in the sodium salt formwas filtered off and washed with water, and then with ether. It was then distributed between 2-butanone and 5% HCl. The organic phase was withdrawn, dried and concentrated under reduced pressure. After recrystallization from acetone/H2O, 8.4 g of a pure product (84% from the methoxy compound), m.p. 224°-226° was obtained.
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