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

HRID 1508896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1508896
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 18423131Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoateAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-94a6a672922d43ab934a3fdb81c2cd66
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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