K. Kikushima et al. / Tetrahedron 66 (2010) 6906e6911
6911
layer was dried over MgSO4, filtered, and evaporated. Column
chromatography (SiO2, AcOEt/hexane¼1/4 v/v) gave 1,2-dibromo-
3-phenylpropane in 93% yield.
(center of excellence) Program ‘Global Education and Research
Center for Bio-Environmental Chemistry’ of Osaka University.
4.8. A typical procedure for bromination of ketone: ethyl
2-bromo-3-oxo-3-phenylpropanoate (16e)
Supplementary data
Supplementary data associated with this article can be found, in
In a 5 mL two-necked flask were placed NH4VO3 (2.9 mg,
0.025 mmol) and AlBr3 (72.0 mg, 0.27 mmol). The flask was evac-
uated and backfilled with molecular oxygen. Acetonitrile (1.5 mL)
and 87 mL (0.50 mmol) of ethyl benzoylacetate were added. The
References and notes
mixture was stirred at 80 ꢀC for 18 h, followed by treatment with
1 N HCl aq and extraction with ether. The organic layer was dried
over MgSO4, filtered, and evaporated. Column chromatography
(SiO2, AcOEt/hexane¼1/4 v/v) gave ethyl 2-bromo-3-oxo-3-phe-
nylpropanoate in 95% yield.
ꢀ
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In a 100 mL two-necked flask were placed, NH4VO3 (58.5 mg,
0.50 mmol), AlBr3 (1.47 g, 5.5 mmol). The flask was evacuated and
backfilled with molecular oxygen. 30 mL of 1,4-dioxane and 1.50 g
of 4-tert-butylphenol (10 mmol) were added. The mixture was
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Acknowledgements
One of the authors K.K. acknowledges a JSPS fellowship for
young scientists, and expresses special thanks for the Global COE