1002
H. CHEN, L. SHEN, AND Y. LIN
EXPERIMENTAL
Melting points were determined on an XF-4 apparatus and were uncorrected.
H NMR spectra were recorded on a DPX-400 Bruker FT-NMR spectrometer with
1
tetramethylsilane as internal reference. Unless otherwise indicated, all commercially
available materials were used as received. All products are known and were identified
by comparing their spectral data and physical properties with those of authentic
samples. All yields refer to isolated products.
General Preparation
Methylarene (1 mmol), BBr (1.2 mmol), and 5 mL CCl were reacted at room
3
4
temperature in oven-dry glassware containing a Teflon-coated stirred bar and dry
septum under an argon atmosphere. When the reaction reach the end, as indicated
by thin-layer chromatography (TLC; 25:1 petroleum ether–ethyl acetate), the mix-
ture was quenched with water and extracted with dichloromethane, and the organic
layer was washed with brine and dried over Na SO . The solvent was evaporated in
2
4
vacuum, and the crude product was subjected to column chromatography using
00 to 200-mesh gel as stationary phase and petroleum ether–ethyl acetate (25:1)
as eluent. Finally, the individual product was received.
1
REFERENCES
1
. Trzeciak, A. M. Carbonylation of benzyl bromide to benzeneacetic acid and its esters cat-
alysed by water-soluble palladium complexes. J. Mol. Catal. 2000, 154, 93–101; (b) Zeng, L.
M.; Jung, M. E.; Peng, T. S.; Zeng, H. Y.; Le, Y.; Su, J. Y. Total synthesis of Bao Gong
Teng-A, a natural antiglaucoma compound. J. Org. Chem. 1992, 57, 3528–3530; (c)
Fischer, B.; Chulkin, A.; Boyer, J. L.; Gendron, F. P.; Chapal, J.; Petit, P.; Hillaire-Buys,
0
D.; Harden, K. T.; Beaudoin, A. R. 2-Thiother 5 -O-(1-thiotriphosphate)adenosine deriva-
tives as new insulin secretagogues acting through P
2
Y-receptors. J. Med Chem. 1999, 42,
3636–3646; (d) Vinod, T. K.; Hart, H. Synthesis of self-filled, vaulted, and intracavity func-
tionalized cappedophanes. J. Org. Chem. 1991, 56, 5630–5640; (e) Otsuka, H.; Araki, K.;
Matsmoto, H.; Harada, T.; Skinkai, S. Synthesis and NMR spectroscopic studies of
bridged and capped calix[6]arenes. J. Org. Chem. 1995, 60, 4862–4687; (f) Tadashi, S.;
Moriyasu, A. Studies on heteroaromaticity, XXI: Bromination of 6-substituted uracils with
NBS. Bull. Chem. Soc. Jap. 1968, 41, 2215–2217.
2
. (a) Toba, R.; Kaifer, A. E. Dendritic cavitands: Preparation and electrochemical proper-
ties. Chem. Commun. 2002, 1768–1769; (b) Newcomb, M.; Timko, J. M.; Walba, D. M.;
Cram, D. J. Host–guest complexation, 3: Organization of pyridyl binding sites. J. Am.
Chem. Soc. 1977, 99, 6392–6398.
3
. (a) Dauben Jr., H. J.; McCoy, L. L. N-Bromosuccinimide, I: Allylic bromination, a general
survey of reaction variables. J. Am. Chem. Soc. 1959, 81, 4863–4873; (b) Walling, C.;
Rieger, A. L.; Tanner, D. D. Positive halogen compounds, VIII: Structure and reactivity
in N-bromosuccinimide brominations. J. Am. Chem. Soc. 1963, 85, 3129–3134; (c)
Greenwood, F. L.; Kellert, M. D.; Sedlak, J. 4-Bromo-2-heptene. Org. Synth. Coll. Vol.
4
4
1963, 108; (d) Campaigne, E.; Tullar, B. F. 3-Thenyl-bromide. Org. Synth., Coll. Vol.
1963, 921; (e) Djerassi, C. Brominations with N-bromosuccinimide and related com-
pounds: The Wohl–Ziegler reaction. Chem. Rev. 1948, 43, 271–317; (f) Smith, M. B.;
March, J. Free-radical substitution. In March‘s Advanced Organic Chemistry, 5th ed.,