Water → 1-(4-bromophenyl)butane-1,3-dione

Temperatur

-5 °C

To a suspension of sodium ethoxide (4.49 g, 66 mmol) in EtOAc (10 mL) that was cooled to −5° C. was added a solution of 4-bromoacetophenone (11.94 g, 60 mmol) in EtOAc (10 mL) and THF (10 mL). The mixture was stirred at 0° C. for 4 hours before warming to ambient temperature and stirring for 48 hours. Water (20 mL) and dichloromethane (40 mL) were added and a white precipitate was filtered from the mixture. To the solid was added 2N HCl, with vigorous stirring, to pH 1. EtOAc (100 mL) was added and separated, and the water was washed with EtOAc (2×100 mL). The organic portions were combined, dried (Na2SO4) and concentrated in vacuo to yield the desired compound as a pale yellow, crystalline solid (11.09 g, 76%); 1H-NMR (CDCl3): 2.13 (s, 3H, CH3), 6.07 (s, 1H, ═CH), 7.52 (d, 2H, J=8.7 Hz, Ar-2, Ar-6), 7.67 (d, 2H, J=8.7 Hz, Ar-3, Ar-5).

1. temperaturebefore warming to ambient temperature
2. stirringstirring for 48 hours
3. filtrationa white precipitate was filtered from the mixture
4. additionTo the solid was added 2N HCl
5. additionEtOAc (100 mL) was added
6. customseparated
7. washthe water was washed with EtOAc (2×100 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo

ORD-Eintrag

ord-78030590c14b4524be40003fef1a418c

Quelldatensatz

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07105518B2