Bromine → Ethyl 2-bromo-3-(2,4-dichlorophenyl)-3-oxopropanoate

HRID 1530125ノート

反応式

HRID 1530125 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[Br:17]Br>ClCCl>[Br:17][CH:10]([C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

4

反応物 2

HCID 24408BromineHCID 542007Ethyl 3-(2,4-dichlorophenyl)-3-oxopropanoate

生成物 1

HCID 58094874Ethyl 2-bromo-3-(2,4-dichlorophenyl)-3-oxopropanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of ethyl 3-(2,4-dichlorophenyl)-3-oxopropanoate (3.95 g, 15.1 mmol) in dichloromethane (150 mL) was added a solution of bromine (0.935 mL, 18.2 mmol) in dichloromethane (20.0 mL) dropwise at 0° C. The solution was then stirred at room temperature for 1 hour. The reaction was quenched with 10% aqueous potassium carbonate solution, and then the layers were separated. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude oil was used directly in the next step (5.27 g, quantitative). LCMS: (AA) ES+, 341. 1H NMR (400 MHz, d1-chloroform) (2 sets of signals, keto and enol): 12.78 (s, 1H), 7.73-7.28 (m, 2 sets of 3H), 5.73 (s, 1H), 4.37 (q, J=7.28 Hz, 2H), 4.29 (q, J=7.28 Hz, 2H), 1.41 (t, J=7.03 Hz, 3H), 1.29 (t, J=7.03 Hz, 3H).

後処理

  1. customThe reaction was quenched with 10% aqueous potassium carbonate solution
  2. customthe layers were separated
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-612a2cca36e943c99dc11432f8128fa8
出典データセット
uspto-grants-2015_07
特許番号
US09090601B2

反応ノート

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