Boron tribromide → HCID 51033994, compound

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Reaction Steps

To a solution of 3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-1-(3,4,5-trimethoxy-benzyl)-1,3-dihydro-indol-2-one and 3-[1-(4-chloro-phenyl)-1-phenyl-meth-(Z)-ylidene]-1-(3,4,5-trimethoxy-benzyl)-1,3-dihydro-indol-2-one (317 mg, 0.62 mmol) in dichloromethane (5 ml) was added a solution of boron tribromide (1M in CH2Cl2, 3 ml) at room temperature. The mixture was stirred at room temperature for 5 h. After being quenched by pouring into ice water, the mixture was extracted with ethyl acetate, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with (hexane/ethyl acetate=1/1) to give 3-[1-(4-chloro-phenyl)-1-phenyl-meth-(E)-ylidene]-1-(3,4,5-trihydroxy-benzyl)-1,3-dihydro-indol-2-one (60 mg). 1H NMR (300 Hz, CDCl3): δppm 4.66 (s, 2H), 5.60 (b, 1H), 6.31 (s, 2H), 6.56 (d, 1H), 6.67-6.82 (m, 2H), 7.00-7.23 (m, 8H), 7.38 (d, 2H); and 3-[1-(4-Chloro-phenyl)-1-phenyl-meth-(Z)-ylidene]-1-(3,4,5-trihydroxy-benzyl)-1,3-dihydro-indol-2-one (40 mg). 1H NMR (300 Hz, CDCl3): δppm 4.72 (s, 2H), 5.33 (b, 1H), 6.05 (b, 1H), 6.40 (s, 2H), 6.44 (d, 1H), 6.67 (t, 1H), 6.82 (d, 1H), 7.00 (d, 2H), 7.10-7.15 (m, 3H), 7.23-7.26 (m, 2H), 7.37-7.46 (m, 3H).

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