Benzoyl Peroxide → (E)-4-bromo-3-(6-methyl-pyridin-3-yloxy)-but-2-enoic acid ethyl ester

HRID 19290

반응식

HRID 19290 반응식
[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[C:6](/[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)\[CH3:7])[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[C:6](/[O:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)\[CH2:7][Br:17])[CH3:2]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66893705(E)-3-(6-methyl-pyridin-3-yloxy)-but-2-enoic acid ethyl ester

생성물 1

HCID 66895263(E)-4-bromo-3-(6-methyl-pyridin-3-yloxy)-but-2-enoic acid ethyl ester수율 44%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a stirred mixture of (E)-3-(6-methyl-pyridin-3-yloxy)-but-2-enoic acid ethyl ester (3.50 g, 0.016 mol) in carbon tetrachloride (25 mL) under a nitrogen atmosphere was added N-bromosuccinimide (4.23 g, 0.024 mol) and benzoyl peroxide (383 mg, 0.002 mol). Nitrogen gas was bubbled through the mixture for 5 min, and the resulting mixture was heated to reflux for 4 h. The reaction mixture was then placed in the refrigerator overnight. The solids formed were removed by filtration and the filtrate concentrated in vacuo. The crude product obtained was purified using flash column chromatography (silica gel (100-200 mesh), ethyl acetate/hexanes) to afford (E)-4-bromo-3-(6-methyl-pyridin-3-yloxy)-but-2-enoic acid ethyl ester (2.10 g, 44%) as a yellow oil.

후처리

  1. customNitrogen gas was bubbled through the mixture for 5 min
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 4 h
  4. customwas then placed in the refrigerator overnight
  5. customThe solids formed
  6. customwere removed by filtration
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe crude product obtained
  9. customwas purified

출처 및 근거

ORD 기록
ord-57f19c9e0484430786959c3b60c94e7e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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