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

HRID 2212881노트

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HRID 2212881 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 7466p-BromoacetophenoneHCID 2723922Sodium ethoxide

생성물 1

HCID 4326531-(4-bromophenyl)butane-1,3-dione

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

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온도
-5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78030590c14b4524be40003fef1a418c
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105518B2

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