Hydrogen Bromide → 1-Bromo-2-(1,3-dimethylbutyl)benzene

HRID 1645384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645384
[CH3:1][CH:2]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1N)[CH2:3][CH:4]([CH3:6])[CH3:5].[BrH:14].N([O-])=O.[Na+].[OH-].[Na+]>C(O)(=O)C.[Cu].O>[Br:14][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[CH:2]([CH3:1])[CH2:3][CH:4]([CH3:6])[CH3:5]

Komponenten

8

Edukt 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 115284412-(1,3-Dimethylbutyl)anilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 252085081-Bromo-2-(1,3-dimethylbutyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

28.4 g of 2-(1,3-dimethylbutyl)aniline in 134.9 g (667 mmol) of 40 percent hydrobromic acid in glacial acetic acid at 10° C. are admixed with 12.5 g (181 mmol) of sodium nitrite in portions with stirring within 1.5 h. Thereafter, 0.5 g of copper powder is added and the mixture is boiled under reflux for 1 h hour. Subsequently, 120 ml of water and sodium hydroxide solution are added until pH 12 is attained, and the organic phase is removed, washed with dilute hydrochloric acid and concentrated by evaporation under reduced pressure. After distillation in a Kugelrohr apparatus at 0.3 mbar/70° C. and purification of the main fraction by means of preparative HPLC, 8.3 g of a yellowish oil with a purity of 99.4% (determined by HPLC) are obtained.

Aufarbeitung

  1. customat 10° C.
  2. temperatureunder reflux for 1 h hour
  3. customthe organic phase is removed
  4. washwashed with dilute hydrochloric acid
  5. concentrationconcentrated by evaporation under reduced pressure
  6. distillationAfter distillation in a Kugelrohr apparatus
  7. customat 0.3 mbar/70° C. and purification of the main fraction by means of preparative HPLC, 8.3 g of a yellowish oil with a purity of 99.4% (determined by HPLC)
  8. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-e9e945602ffb4c7fa1785ca009c6af75
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124786B2

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