[CH2:1]([O:8][C:9]1[C:10](O)=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:33])=O>>[CH2:1]([O:8][C:9]1[C:10]([Cl:33])=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A mixture of XXIII (3.3 g, 12.2 mmol), diethyl aniline (1.94 mL, 12.2 mmol), and phosphorus oxychloride (0.758 mL, 8.13 mmol) was heated in a 100° C. oil bath for 3 hr. The dark reaction mixture was vacuum distilled to give the product as a clear oil (1.0 g, 28.4%).
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