Aniline → HCID 178507742, compound

Participants

Reaction Steps

Diazonium salt 1 (11.1 mg, 0.0349 mmol) and aniline (32.0 mg, 0.344 mmol) were dissolved in 0.19 g of 95% ethanol. After 20 d, the solution was filtered through Celite 545. Evaporation of the solvent gave an orange oil, which was purified by SiO2 column chromatography (8:2 hexane/ethyl acetate) and following preparative TLC (SiO2, CH2Cl2) afforded 27e as orange crystals (2.5 mg, 22%); m.p. 153.0-154.5° C. IR (ATR): {tilde over (v)}=3417, 2915, 1666, 1628, 1603, 1507, 1398, 1302, 1148, 1092, 834 cm−1. MS (GC, EI): m/z=323 [M+], 197, 120, 94, 65. 1H NMR (500 MHz, CDCl3): δ=7.88-7.82 (m, 6H), 6.76 (d, J=8.8 Hz, 2H), 2.20 (br. s, 1H) ppm. 13C NMR (125 MHz, CDCl3): δ=154.1 (C), 150.5 (C), 145.3 (C), 126.9 (2CH), 125.8 (2CH), 122.2 (2CH), 114.5 (2CH) ppm. 19F NMR (470 MHz, CDCl3): δ=84.4 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm.

Provenance & Evidence