Potassium Carbonate → HCID 80107634, Verbindung

Temperatur

40 °C

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).

1. temperatureThe reaction mixture was then cooled to ambient temperature
2. customThe organic layer was separated
3. washwashed with water (50 mL)
4. customThe organic layer was separated
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto afford the crude product residue
9. customThe crude product residue was purified by column chromatography on silica (0-100% ethyl acetate/hexanes)

ORD-Eintrag

ord-ff6865271c884b38a168c6098984523c

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242984B2