[CH3:1][O:2][C:3](=[O:28])[C:4]1[C:9]([CH:10]=CC2C=CC=CC=2)=[CH:8][C:7]([F:18])=[C:6]([F:19])[C:5]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27].CC([OH:33])(C)C.C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[C:9]([CH:10]=[O:33])=[CH:8][C:7]([F:18])=[C:6]([F:19])[C:5]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27]
A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-6-styrylbenzoic acid methyl ester (1.20 g, 3.00 mmol), 2.5% OSO4 solution in t-BuOH (2.0 mL, 0.165 mmol) and NMO (0.435 g, 3.60 mmol) in 30 mL of 1:1 THF/water was stirred for 1 hour. Sodium periodate (0.963 g, 4.50 mmol) was added. After 1 hour, the reaction mixture was diluted with ethyl acetate and water and the layers separated. The organic layer was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography (1:1 methylene chloride/hexanes) gave 0.406 g (42%) pure desired product.
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