N-bromobutanimide → 1-Bromo-2-(bromomethyl)-3-nitrobenzene

HRID 901856

Reaktionsgleichung

Reaktionsgleichung von HRID 901856
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH2:11][Br:12]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 1235372-Bromo-6-nitrotoluene

Produkt 1

HCID 150631701-Bromo-2-(bromomethyl)-3-nitrobenzeneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A solution of 1-bromo-2-methyl-3-nitro-benzene (16.095 g, 74.5 mmol), 1-Bromo-pyrrolidine-2,5-dione (13.26 g, 74.5 mmol), benzoyl peroxide (180 mg, 0.74 mmol) in CCl4(100 ml) was heated under reflux overnight. After removing the solvent by using rotary evaporator, the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo and resulting brown residue was purified by flash chromatography to give 1-bromo-2-bromomethyl-3-nitro-benzene as a yellow solid (17.55 g, 80%). 1H NMR (CDCl3, 300 MHz) δ: 4.89(s, 2H), 7.35(dd, 1H, J1=J2=8.1 Hz), 7.88(dd, 2H, J1=1.6 Hz, J2=8.1 Hz).

Aufarbeitung

  1. temperatureunder reflux overnight
  2. customAfter removing the solvent
  3. customevaporator
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialAfter drying over MgSO4
  7. concentrationthe organic fraction was concentrated in vacuo
  8. customresulting brown residue
  9. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12e466c0019e4b88a45063cd753063bf
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365063B2

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