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

HRID 2212881Notes

Reaction equation

[O-:1][CH2:2][CH3:3].[Na+].[CH3:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)=[O:7].O.ClCCl>CCOC(C)=O.C1COCC1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH2:5][C:2](=[O:1])[CH3:3])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: -5 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-78030590c14b4524be40003fef1a418c
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105518B2

Reaction notes

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