Potassium Carbonate → N,N-Diphenyl-6-bromo-2-naphthylamine

関与物質

反応手順

A mixture of N-phenyl-6-bromo-2-naphthylamine (29.8 g. 0.10 moles), iodobenzene (50 g. 0.245 mol.), potassium carbonate (60 g. 0.434 mol.), copper bronze (4.0 g. 0.063 g. atoms), 18-crown-6 (3.7 g. 0.014 mol.) and dichlorobenzene (100 ml) was kept under reflux for 3 hours under nitrogen, cooled and filtered. The residue remaining after concentration of the filtrate, was chromatographed over 600 g of silica gel. Elution with toluene-heptane (1:9), gave the product, 28.65 g., m.p. 135.8-137.4° C., in 77% yield. Mass Spec: m/z 373, 375 (M+), 421 (M+ iodo). The product was contaminated with a small amount of the corresponding iodo compound. A sample recrystallized from heptane, m.p. 137.9-139.2° C. was analyzed. Analysis calculated for C22H16NBr: C, 70.59; H, 4.31; N, 4.09; Br, 21.35. Found: C, 69.23; H, 4.22; N, 3.61; Br, 20.56.

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