N-bromobutanimide → Methyl 1-(4-(bromomethyl)phenyl)cyclopropanecarboxylate

HRID 2170619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170619
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:1]1[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylate

Produkt 1

HCID 57443306Methyl 1-(4-(bromomethyl)phenyl)cyclopropanecarboxylateAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-(p-tolyl)cyclopropanecarboxylate (622 mg, 3.27 mmol) in carbon tetrachloride (16 mL) was added N-bromosuccinimide (611 mg) followed by benzoyl peroxide (40 mg). The resulting solution was heated at reflux overnight, and then diluted with methylene chloride. The mixture was washed with brine, dried on MgSO4, and concentrated to afford a colorless oil (860 mg, 97%).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with brine
  4. customdried on MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1017ed48bbb74551815cae6c241a20de
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051265B2

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