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

HRID 1508896ノート

反応式

HRID 1508896 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-94a6a672922d43ab934a3fdb81c2cd66
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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