[H-].[Na+].[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]#[CH:13])=[CH:8][C:7]([N:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[CH:16]=[N:15]2)=[C:6]([F:23])[CH:5]=1.[Br:24]Br.O>O1CCCC1>[Cl:3][C:4]1[C:9]([O:10][CH2:11][C:12]#[C:13][Br:24])=[CH:8][C:7]([N:14]2[C:19](=[O:20])[N:18]([CH3:21])[C:17](=[O:22])[CH:16]=[N:15]2)=[C:6]([F:23])[CH:5]=1
To a stirred mixture of 0.05 g (0.002 mole) of sodium hydride in 5 mL of tetrahydrofuran was added a solution of 0.55 g (0.0018 mole) of 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione (Compound 21, see Example III, Step J) in 5 mL of tetrahydrofuran. To this mixture was added a solution of 0.28 g (0.0018 mole) of bromine in 5 mL of tetrahydrofuran. After complete addition, the reaction mixture was stirred at room temperature for one hour. Water, 5 mL, was added to the mixture, and the total stirred at room temperature for two days. The mixture was partitioned between water and ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 0.45 g of 2-[4-chloro-2-fluoro-5-(3-bromo-2-propynyloxy)phenyl]-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione as a solid (mp 127°-129° C.), Compound 48 in the tables.
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