Hydrogen Bromide → HCID 71062920, compound

Participants

Reaction Steps

Aqueous HBr (70 mL) was added to 4A (7 g, 24.13 mmol) and the reaction mixture was refluxed for 4 h. The reaction mixture was then brought to room temperature, diluted with water and extracted with ethyl acetate (2×100 mL). The organic layers were dried over sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified using flash chromatography using 40% ethyl acetate in hexanes to afford the title compound (5 g, 83.6%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 12.0 (s, 1H), 10.3 (s, 1H), 7.8 (d, J=8.4 Hz, 1H), 6.7 (d, J=7.4 Hz, 1H), 6.6 (s, 1H), 3.0 (m, 1H), 2.7 (m, 2H), 2.4 (m, 2H), 1.9 (m, 1H), 1.7-1.5 (m, 2H), 0.9 (t, J=7.6 Hz, 3H). ESI-MS m/z=247 (M−H)−.

Provenance & Evidence