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

HRID 2212881ノート

反応式

HRID 2212881 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
-5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-78030590c14b4524be40003fef1a418c
出典データセット
uspto-grants-2006_09
特許番号
US07105518B2

反応ノート

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