Water → HCID 13163448, compound

Participants

Reaction Steps

1-(5-bromo-2-hydroxyphenyl)ethanone (7.1 g, 33 mmol) and phenylhydrazine (4.3 g, 40 mmol) were stirred in 45 mL of dry ethanol. Acetic acid (27 drops) was added and the mixture was refluxed for 5 hours. After cooling to room temperature, the precipitates were collected by filtration to provide the crude product as a light yellow solid, which was stirred in 100 mL of xylene and 50 g of polyphosphoric acid at 85° C. for 8 hours. Water was added to the warm crude, and then the mixture was stirred for 10 minutes before poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (petroleum ether:EtOAc=10:1) provided 4-bromo-2-(1H-indol-2-yl)phenol as a light yellow powder (2.1 g, 22.1%). 1H-NMR (CDCl3, 400 MHz) δ 10.08 (s, 1H), 9.56 (s, 1H), 7.88 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.14˜7.19 (m, 2H), 7.08 (t, J=7.2 Hz, 1H), 6.8˜56.88 (m, 2H). MS (M+H)+: 288/290.

Provenance & Evidence