Phenylacetylene → 5-bromo-2-phenyl-1H-indole

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Reaction Steps

The general procedure was used to convert 4-bromo-2-iodobenzenamine and phenylacetylene to the title product. Purification by flash chromatography gave the analytically pure product as a white solid, 60% yield. 1H NMR (300 MHz, DMSO) δ 11.77 (s, 1H), 7.88-7.85 (d, J=7.4, 2H), 7.72 (s, 1H), 7.50-7.45 (t, J=7.5, 2H), 7.39-7.35 (m, 2H), 7.23-7.20 (dd, J=8.5, 1.8, 1H), 6.89 (s, 1H). 13C NMR (75 MHz, DMSO) δ 139.06, 135.69, 131.54, 130.41, 128.88, 127.78, 125.09, 123.89, 122.04, 113.15, 111.78, 98.16. Anal. Calcd. for C14H10BrN: C, 61.79; H, 3.70; Br, 29.36; N, 5.15. Found C, 61.60; H, 3.74; N, 5.02.

Provenance & Evidence