Triethylamine → HCID 57791832, compound

Participants

Reaction Steps

(6-bromo-3-oxo-1,3-dihydroisobenzofuran-1-yl)triphenylphosphonium bromide (95) (9.0 g, 16.24 mmol) and 2-fluoro-5-formylbenzonitrile (2.91 g, 19.49 mmol) were dissolved DCM (60 mL), to this was added triethylamine (2.94 mL, 21.11 mmol) and the reaction was stirred overnight. The reaction mixture was quenched with water (50 mL), extracted with DCM (2×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford an orange gum. This was passed through a plug of silica eluting with ethyl acetate to afford a yellow gum. To this was added water (40 mL), EtOH (40 mL) and DMF (4 mL). Hydrazine hydrate (8.13 g, 162.39 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled and the precipitate was collected by filtration, washed with EtOH (25 mL) and air dried to afford the desired compound as a white solid (2.410 g, 41.4% yield), which was used without further purification; 1H NMR (400.132 MHz, DMSO) δ 4.38 (2H, s), 7.48 (1H, t), 7.75-7.71 (1H, m), 7.89 (1H, dd), 8.02 (1H, d), 8.18 (1H, d), 8.22 (1H, s), 12.64 (1H, s); m/z (LC-MS, ESI−), RT=2.18 (M−H 358).

Provenance & Evidence