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

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Reaction Conditions

Reaction Steps

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (352 mg, 1.16 mmol) and 3,5-lutidine (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 406 mg of the title compound. Yield: 85%. 1H NMR (300 MHz, CDCl3) δ 1.45 (m, 2H), 1.70 (m, 2H), 2.08 (m, 2H), 2.53 (s, 6H), 2.63 (t, J=7.8 Hz, 2H), 4.84 (t, J=7.5 Hz, 2H), 7.18-7.58 (m, 9H), 7.93 (s, 1H), 9.21 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 18.6, 25.8, 30.8, 31.9, 35.2, 61.3, 126.8, 126.9, 127.0, 128.7, 128.8, 138.4, 138.7, 140.7, 141.1, 141.7, 146.0 ppm.

Provenance & Evidence