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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (322 mg, 1.06 mmol) and 3,4-lutidine (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 380 mg of the title compound. Yield: 87%. 1H NMR (300 MHz, CDCl3) δ 1.43 (m, 2H), 1.69 (m, 2H), 2.05 (m, 2H), 2.46 (s, 3H), 2.48 (s, 3H), 2.62 (t, J=7.5 Hz, 2H), 4.82 (t, J=7.2 Hz, 2H), 7.18-7.58 (m, 9H), 7.76 (d, J=6.3 Hz, 1H), 9.07 (d, J=6.3 Hz, 1H), 9.29 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 17.1, 20.4, 25.6, 30.7, 31.7, 35.2, 60.7, 126.8, 126.9, 127.0, 128.4, 128.7, 128.8, 138.2, 138.5, 140.7, 141.1, 141.7, 143.3, 157.4 ppm.

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