1-(4-Nitrophenyl)-1-octyne
Bruce A. Hathaway* and Steven W. Blanner
Department of Chemistry, Southeast Missouri State University, MS 6400, One University Plaza, Cape Girardeau, Missouri, 63701, USA. Tel. 001 573-651-2370; Fax 001 573-986-6433; E-mail: [email protected]
Received: 27 June 2000 / Accepted: 17 July 2000 / Published: 30 July 2000
Following the procedure of Takahashi, et al (1), to a mixture of 1-iodo-4-nitrobenzene (7.76 mmol, 1.90g) and 1-octyne (9.3 mmol, 1.023g) in diethylamine (40 mL) are added bis[triphenylphosphine]palladium dichloride (0.2mmol, 0.14g) and copper(I) iodide (0.1mmol, 0.01g). The reaction is stirred at room temperature under a nitrogen atmosphere for 24 hours. The solvent is then removed by rotary evaporation. The remaining solution is suspended in petroleum ether. The resulting suspension is filtered, and the solvent removed. The crude oily product is purified by means of column chromatography using a 19:1 petroleum ether: diethyl ether as the eluent. Yield: 1.17g (65.6%)
IR (NaCl plates, cm-1): 3080, 2931, 2858, 2227, 1594, 1518, 1342, 1108, 854, 750, 734, 688.
1H-NMR (300 MHz, CDCl3): 0.83 (3H, t, J=6.87 Hz), 1.25 (4H, m), 1.38 (2H, m), 1.53 (2H, q, J=7.38 Hz), 7.43 (2H, d, J=8.94), 8.07 (2H, d, J=8.94).
13C-NMR (75.5 MHz, CDCl3): 146.88, 132.52, 131.56, 123.73, 97.08, 79.62, 31.69, 28.99, 28.76, 22.91, 19.88, 14.34.
GC-MS (ion trap, m/e, in order of decreasing peak size): 128, 142, 232 (M + 1), 202, 115, 116, 156, 215, 102, 188.
Reference
1. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
Sample Availability: available from MDPI. MDPI 18996.
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