Carbon Tetrachloride → 4,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

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Reaction Steps

A mixture composed of 2,9,-dimethyl-4,7-diphenyl-1,10-phenanthroline (4.0 g, 0.011 mole), N-chlorosuccinimide (9.0 g, 0.067 mole), benzoyl peroxide (0.011 g) and 96 ml carbon tetrachloride was stirred for 6 hr in an oil bath at 90°. After standing overnight at 4° C., crystals of succinimide were removed by filtration. The solvent was removed from the filtrate by vacuum evaporation to produce a light yellow solid which was then dissolved in chloroform. The organic layer was washed with saturated sodium carbonate solution and dried over anhydrous magnesium sulfate. Removal of solvent by vacuum evaporation yielded the white solid product. Yield=6.1 g (97%). Mp=286°-289°. IR 3020-3080, 1620, 1570, 1550, 1490, 1445, 1405, 1360, 1220, 1040, 930, 895, 835, 800, 780, 760, 735, 700, 620 cm-1. 60 MHz proton NMR in CDCl3 δ7.55 singlet (10 protons), δ8.05 singlet (2 protons), δ8.3 singlet (2 protons).

Provenance & Evidence