N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate

HRID 1508896노트

반응식

HRID 1508896 반응식
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].C1C(=O)N([Br:22])C(=O)C1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:2]([CH3:1])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 13296592Methyl 2-methyl-2-(4-methylphenyl)propanoate

생성물 1

HCID 18423131Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate수율 62.4%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A 500-mL round bottom flask, with stirrer bar, was charged with methyl 2-methyl-2-(p-tolyl)propanoate (2.50 g, 13.0 mmol), NBS (2.31 g, 13.0 mmol), and carbon tetrachloride (240 mL). The resulting solution was heated at reflux and AIBN (0.043 g, 0.26 mmol) was added. After stirring for 3.5 h, the reaction was cooled to room temperature and the solids removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica using hexane/ethyl acetate (100:0 to 80:20) as eluent as eluent to afford the title compound (2.20 g, 62%) as a colorless oil. MW=271.15. 1H NMR (CDCl3, 300 MHz) δ 7.39-7.28 (m, 4H), 4.48 (s, 2H), 3.65 (s, 3H), 1.57 (s, 6H).

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux
  3. customthe solids removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica

출처 및 근거

ORD 기록
ord-94a6a672922d43ab934a3fdb81c2cd66
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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