H. Adibi et al. / Tetrahedron Letters 48 (2007) 1255–1259
1259
BTPPMS was prepared according to our previously
reported procedures.
Hajipour, A. R.; Mahboubkhah, N. Org. Prep. Proced.
Int. 1999, 31, 112; (c) Meunier, B. New J. Chem. 1992, 16,
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Soc. 2002, 23, 773; (b) Tamhankar, B. V.; Desai, U. V.;
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Acknowledgements
We gratefully acknowledgment the Kermanshah Uni-
versity of Medical Sciences Research Council for the
financial support. We are also thankful of the Isfahan
University of Technology (IUT), Iran, for the financial
support. Further financial support from the Center of
Excellency in Chemistry Research (IUT) is gratefully
acknowledged.
1
8. (a) Hajipour, A. R.; Mallakpour, S. E.; Adibi, H.
Phosphorus, Sulfur Silicon 2000, 167, 71; (b) Hajipour,
A. R.; Mallakpour, S. E.; Adibi, H. Chem. Lett. 2000, 460;
(c) Hajipour, A. R.; Mallakpour, S. E.; Mohammadpoor-
Baltork, I.; Adibi, H. Phosphorus, Sulfur Silicon 2000, 165,
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55; (d) Hajipour, A. R.; Mallakpour, S. E.; Mohammad-
poor-Baltork, I.; Adibi, H. Synth. Commun. 2001, 31,
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madpoor-Baltork, I.; Adibi, H. Synth. Commun. 2001, 31,
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madpoor-Baltork, I.; Adibi, H. Monatsh. Chem. 2003, 134,
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Chem. Lett. 2001, 164; (h) Hajipour, A. R.; Mallakpour,
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26. Representative procedure for the oxidative bromination of 2-
methoxynaphthalene 1c. To a solution of BTPPMS
(10 mmol, 4.66 g) and potassium bromide (10 mmol,
1.19 g) in acetonitrile (50 mL) in a 250 mL round-bot-
tomed flask, 2-methoxynaphthalene 1c (10 mmol, 1.58 g)
was added. The reaction mixture was stirred at room
temperature for 2 h. After disappearance of the starting
phenol as monitored by TLC using EtOAc/cyclohexane
(2:8), the mixture was filtered through a sintered glass
funnel and the solid residue was washed with acetonitrile
(50 mL). The organic layers were combined and washed
successively with 5% aqueous sodium thiosulfate solution
12. Clark, J. H.; Ross, J. C.; Macquarrie, D. J.; Barlow, S. J.;
Bastock, T. W. J. Chem. Soc., Chem. Commun. 1997, 1203.
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1
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6. For recent work using Oxone as an oxidant, see: (a)
2 4
(100 mL), dried over Na SO and concentrated. The crude
product was crystallized from ethanol to afford 1-bromo-
2-methoxynaphthalene as solid needles in a 89% yield, mp
Ò
1
2
2
Hajipour, A. R. Indian J. Chem. 1997, 36B, 1069; (b)
83–84 °C (lit. mp 85 °C).