4-Hydroxybenzaldehyde → HCID 86611514, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxy benzaldehyde (4.22 g, 34.6 mmol) and 2,5-dibromopyridine (8.19 g, 34.6 mmol) in dimethylacetamide (100 mL) is added K2CO3 (11.95 g, 86.4 mmol) at RT. The reaction mixture is warmed to 130° C. for 8 h. The reaction mixture is then poured into H2O (200 mL) and saturated NaHCO3 (100 mL), extracted with EtOAc (3×200 mL), and then the combined extracts are washed with saturated NaHCO3, brine, dried over MgSO4, filtered, and concentrated. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 5% of ethyl acetate to 25% of ethyl acetate giving ethyl 4-(5-Bromo-pyridin-2-yloxy)-benzaldehyde (3.50 g, 36%) as a white solid. 1NMR (400 MHz, CDCl3) δ ppm: 9.96 (s, 1H), 8.23 (d, J=2.6 Hz, 1H), 7.93-7.90 (m, 2H), 7.83 (ds, J=2.6, 8.4 Hz, 1H), 7.27-7.24 (m, 2H), 6.92 (d, J=7.9 Hz, 1H); MS (ES): [M+H]+ found 277.7.

Provenance & Evidence