Hydrogen Bromide → 5-Bromo-2-(2-methylpropyl)benzonitrile

HRID 1942631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942631
N[C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8].[BrH:14].N([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.O.[Cu](Br)Br.[Cu]Br>[Br:14][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8]

Komponenten

9

Edukt 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 222279325-Amino-2-(2-methylpropyl)benzonitrileHCID 23668193Sodium Nitrite

Produkt 1

HCID 513581655-Bromo-2-(2-methylpropyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24593copper(I) bromideKatalysatorHCID 24611Copper bromide (CuBr2)KatalysatorHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-2-isobutylbenzonitrile (D57) (34 g) in acetonitrile (500 mL) was added HBr (24.37 mL) at 0° C. Then a solution of sodium nitrite (16.16 g) in water (50 mL) was added to the reaction mixture. After stirring for 30 min, copper(II) bromide (87 g) and copper(I) bromide (5.60 g) were added to the reaction mixture. The mixture was stirred at room temperature for 16 h. Saturated aqueous sodium bicarbonate solution was added to quench the reaction. The mixture was extracted with EA. The combined organic solution was dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography to give 5-bromo-2-(2-methylpropyl)benzonitrile (D58) (36 g) as a colorless oil. 6H (CDCl3, 400 MHz): 0.96 (6H, d), 1.98 (1H, m), 2.69 (2H, d), 7.18 (1H, d), 7.64 (1H, dd), 7.55 (1H, d).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with EA
  5. dry with materialThe combined organic solution was dried over anhydrous sodium sulphate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8b86e56db2c84ed3a0c9ac1afcf6695d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389508B2

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