Methyl o-toluate → Methyl 2-(bromomethyl)benzoate

HRID 225986

Reaktionsgleichung

Reaktionsgleichung von HRID 225986
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 2

HCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Produkt 1

HCID 2734813Methyl 2-(bromomethyl)benzoateAusbeute 95.246,602 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a mixture of methyl 2-methylbenzoate (5.0 g, 0.033 mmol) and N-bromosuccinimide (5.9 g, 0.033 mmol) in CCl4 (50 mL) was added benzoyl peroxide (0.04 g, 0.00016 mmol). The mixture was heated to reflux for 1.5 h, cooled to room temperature, filtered through Celite, and concentrated to afford methyl 2-(bromomethyl)benzoate (7.2 g, ca. 94% mass recovery), which was contaminated with ca. 14% unreacted starting material and was used without purification.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. filtrationfiltered through Celite
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cf3f803730124b61b67889dd940bee60
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557135B2

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