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

HRID 1530125노트

반응식

HRID 1530125 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-612a2cca36e943c99dc11432f8128fa8
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090601B2

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