248 JOURNAL OF CHEMICAL RESEARCH 2012
Bromo-3-nitrostyrene (9):21,28 IR: νmax: 1528, 1351, 939, 754 cm−1,
1H NMR (400 MHz, CDCl3) δ 8.57 (s, 0.29H, Z-isomer), 8.18 (m,
1.70H), 8.01 (d, J = 7.6 Hz, 0.29H, Z-isomer), 7.66–7.50 (m, 1.82H),
7.18 (m, 1H, 0.71H, E-isomer, 0.29H, Z-isomer), 7.00 (d, J = 14.1 Hz,
0.71H, E-isomer), 6.66 (d, J = 8.2 Hz, 0.29H, Z-isomer).
In conclusion, direct conversion of cinnamic acids to the
corresponding bromoalkenes was achieved by using IBX in
combination with TBAB in acetonitrile–water (2:1, v/v).
(E)-1-(β-Bromovinyl)naphthalene (10): Oil29,30 IR: νmax: 1588, 935,
Experimental
IR spectra were recorded on a BrukerALPHA FT-IR Spectrometer. 1H
NMR (400 MHz) and 13C NMR (100 MHz) were robtained with a
Bruker Avance III 400 MHz spectrometers with CDCl3 as solvent and
tetramethylsilane (TMS) as internal standard. Chemical shifts were
reported in ppm. All coupling constants (J values) were reported
in Hertz (Hz). HRMS was performed on Waters Micromass GCT.
Preparative TLC (20×20 cm) was preformed on Silica Gel 60 F254.
IBX used were prepared according to the literature.20
1
781 cm−1; H NMR (400 MHz, CDCl3) δ 8.09 (d, J = 8.7 Hz, 1H),
7.98–7.85 (m, 3H), 7.66–7.45 (m, 4H), 6.83 (d, J = 13.7 Hz, 1H);
13C NMR (101 MHz, CDCl3) δ 135.09, 133.67, 133.62, 130.65,
128.87, 128.63, 126.56, 126.21, 125.63, 124.31, 123.80, 108.60.
This work was supported by National Natural Science Founda-
tion of China (20972109).
General procedure
Received 10 January 2012; accepted 23 February 2012
Paper 1201098 doi: 10.3184/174751912X13324352705972
Published online: 10 May 2012
Cinnamic acid (37.0 mg, 0.25 mmol), IBX (84 mg, 0.3 mmol), TBAB
(105 mg, 0.3 mmol) were added to acetonitrile–water (3 mL, 2:1 v/v)
in succession, then the mixture was stirred at 80 °C. The progress of
the reaction was monitored by TLC (PE/EtOAc/AcOH, 10/1/0.5).
After completion of the reaction, when the mixture was cool to rt,
ethyl acetate (10 mL) was added to the solution. The organic layer
was washed with brine (10 mL), dried over MgSO4 and the solvent
evaporated in vacuo. The crude product was purified by preparative
TLC (eluent: PE–EtOAc, 10:1) to give the product.
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1
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1
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