W. M. Seganish et al. / Tetrahedron 61 (2005) 2117–2121
2121
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3.2.10. 2,3,4-Trimethoxybromobenzene. Pyridinium
hydrobromide perbromide (90%) (4.66 g, 13.1 mmol), was
added in small portions over 30 min to a light red solution of
1,2,3-trimethoxybenzene (2.00 g, 11.9 mmol) and FeCl3$
6H2O (50 mg 0.18 mmol) in Ac2O (35 mL). The deep red
solution was then heated at 55 8C for 5 min. The reaction
was carefully poured into 100 mL of hot water. After
cooling, the mixture was extracted with 50 mL of Et2O
(!4), dried (MgSO4), and evaporated to yield a yellow oil.
Column chromatography (TLC RfZ0.44, 4:1 hexanes/
EtOAc) produced a pale yellow oil (92%). IR (CCl4) 3009
(m), 2960 (m), 2940 (s), 2898 (m), 2836 (m), 1580 (m),
1486 (s), 1462 (s), 1414 (s), 1293 (s), 1221 (s), 1096 (s),
1017 (s). 13C NMR (CDCl3) d 56.2, 61.0, 61.1, 108.4, 108.6,
126.8, 151.0, 152.2, 153.3. The 1H NMR spectral data
matches that reported by Pettit.37
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Acknowledgements
We thank the National Institutes of Health, Cancer Institute
(CA 82169-01) and the University of Maryland for generous
financial support. W.M.S thanks the Organic Division of the
American Chemical Society for a Graduate Fellowship
(Procter and Gamble). We also thank Dr. Yiu-Fai Lam
(NMR) and Noel Whittaker (MS) for their assistance in
obtaining spectral data.
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