Benzoyl Peroxide → Methyl 2-(bromomethyl)-5-methylbenzoate

HRID 2361330

Reaktionsgleichung

Reaktionsgleichung von HRID 2361330
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[Br:13][CH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 273300Methyl 2,5-dimethylbenzoate

Produkt 1

HCID 57561371Methyl 2-(bromomethyl)-5-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A light yellow, homogeneous solution of methyl 2,5-dimethylbenzoate (4.467 g, 27.2 mmol), 1-bromopyrrolidine-2,5-dione (4.84 g, 27.2 mmol) and benzoic peroxyanhydride (0.659 g, 2.72 mmol) in benzene (136 mL) under nitrogen was refluxed. After 8.5 hr, the reaction was cooled to room temperature. The succinimide was filtered, rinsed with benzene and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and washed with water (50 mL) and brine (50 mL), dried over MgSO4, and concentrated in vacuo to give crude product that was a mixture of the desired product and its regioisomer. This crude product was used in the next step without further purification.

Aufarbeitung

  1. filtrationThe succinimide was filtered
  2. washrinsed with benzene
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. washwashed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto give crude product that

Quellen und Nachweise

ORD-Eintrag
ord-040ee3d87076419c8368eb5cc395869e
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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