Potassium Carbonate → HCID 80107634, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1H-pyrazole (500 mg, 3.40 mmol), 4-(chloromethyl)phenyl acetate (659 mg, 3.57 mmol), and potassium carbonate (1.18 g, 8.50 mmol) was diluted with DMF (5 mL) at ambient temperature. The reaction mixture was heated to 40° C. for 4 hours. The reaction mixture was then diluted with sodium hydroxide (2.0 M in water, 3.40 mL, 6.80 mmol) and stirred for an additional 30 minutes at 40° C. The reaction mixture was then cooled to ambient temperature and diluted with ethyl acetate (200 mL) and saturated aqueous ammonium chloride solution (50 mL). The organic layer was separated and washed with water (50 mL) and then brine (25 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by column chromatography on silica (0-100% ethyl acetate/hexanes) to afford 4-((4-bromo-1H-pyrazol-1-yl)methyl)phenol. MS ESI calc'd. for C10H10BrN2O [M+H]+ 253 and 255. found 253 and 255. 1H NMR (500 MHz, DMSO-d6) δ 9.45 (s, 1H), 7.98 (s, 1H), 7.51 (s, 1H), 7.08 (d, J=8.5 Hz, 2H), 6.69 (dd, J=7.0 Hz, 2.0 Hz, 2H), 5.14 (s, 2H).

Provenance & Evidence