2-Methylpyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-2-methyl-pyridinium bromide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (358 mg, 1.18 mmol) and 2-picoline (1 mL) was heated at 60-70° C. for 12 hrs. The resulting 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 393 mg of the title compound. Yield: 84%. 1H NMR (300 MHz, CDCl3) δ 1.53 (m, 2H), 1.71 (m, 2H), 1.95 (m, 2H), 2.65 (t, J=7.5 Hz, 2H), 2.92 (s, 3H), 4.83 (t, J=8.1 Hz, 2H), 7.20-7.60 (m, 9H), 7.89-8.02 (m, 2H), 8.38 (d, J=7.5 Hz, 1H), 9.53 (d, J=6.0 Hz, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 20.9, 25.9, 30.6, 30.8, 35.2, 58.3, 126.3, 126.8, 126.9, 127.0, 128.7, 128.8, 130.3, 138.5, 140.7, 140.9, 145.2, 146.3, 154.1 ppm.

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