3-Methylpyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3-methyl-pyridinium bromide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (358 mg, 1.18 mmol) and 3-picoline (1 mL) was heated at 60-70° C. for 12 hrs. The resulted mixture was washed with diethyl ether and then dissolved in water (15 mL). The aqueous solution was extracted with diethyl ether (30 mL×3). Water was removed by lyophilization to afford 421 mg of the title compound. Yield: 90%. 1H NMR (300 MHz, CDCl3) δ 1.45 (m, 2H), 1.70 (m, 2H), 2.08 (m, 2H), 2.59 (s, 3H), 2.63 (t, J=7.5 Hz, 2H), 4.92 (t, J=7.5 Hz, 2H), 7.18-7.58 (m, 9H), 7.94 (t, J=7.2 Hz, 1H), 8.17 (d, J=8.1 Hz, 1H), 9.26 (d, J=6.3 Hz, 1H), 9.46 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 18.8, 25.7, 30.7, 31.9, 35.2, 61.5, 126.8, 126.9, 127.0, 127.7, 128.3, 128.7, 128.8, 138.5, 139.5, 140.7, 141.1, 142.1, 144.5, 145.5 ppm.

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