[Cl:1][C:2]1[C:17]([Cl:18])=[C:16]([OH:19])[CH:15]=[CH:14][C:3]=1[C:4](=[N:12][OH:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1F.C1C=CC=CC=1.[H-].[Na+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C.C1(C)C=CC=CC=1.O>[O:13]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([C:3]2[CH:14]=[CH:15][C:16]([O:19][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:17]([Cl:18])[C:2]=2[Cl:1])=[N:12]1
To a solution of 18.42 g (0.06 m) of 2,3-dichloro-4-hydroxy-2'-fluorobenzophenone oxime of Example 2C in 120 ml of DMF and 120 ml of benzene 3.6 g (0.15 m) of NaH is added. The mixture is brought to a temperature of 80°-85° C. and held there for 3 hours. The mixture is cooled to room temperature and a solution of 11 g (0.066 m) of ethyl bromoacetate in 20 ml of DMF is added dropwise. After addition the mixture is stirred for 1/2 hour. Water is added to decompose excess NaH. The mixture is extracted with ethylacetate, dried (Na2SO4) and evaporated to give 19 g. This is dissolved in toluene and chromatographed on silica gel with toluene as elutant. The product of ethyl 4-(1,2-benzisoxazol-3-yl)-2,3-dichlorophenoxyacetate is isolated from the column, 3.8 g (17%). An analytical sample is recrystallized from 95% ethanol, m.p. 88°-89° C.
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