Hydrogen Bromide → 4-Bromo-4'-chloro-3-methylbiphenyl

HRID 341680

Reaktionsgleichung

Reaktionsgleichung von HRID 341680
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]2[CH:11]=[C:10]([CH3:12])[C:9](N)=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.C(#N)C.N(OCCCC)=O.[BrH:26]>[Cu]Br>[Br:26][C:9]1[CH:8]=[CH:7][C:6]([C:5]2[CH:14]=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:11][C:10]=1[CH3:12]

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 6342AcetonitrileHCID 10996Butyl nitriteHCID 230051884'-Chloro-3-methylbiphen-4-ylamine

Produkt 1

HCID 594505164-Bromo-4'-chloro-3-methylbiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24593copper(I) bromideKatalysator

Versuchsvorschrift

4′-Chloro-3-methylbiphen-4-ylamine (16.5 g, 0.077 mol) is added to acetonitrile (140 ml) and stirred at room temperature until dissolution is complete. The reaction mixture is cooled to between −5° C. and 0° C., tent-butyl nitrite (90%, 12.4 ml, 0.093 mol) is added dropwise and the reaction mixture is maintained at between −5° C. and 0° C. for 30-40 minutes. The mixture is added slowly to a preheated (50° C.) suspension of copper (I) bromide (5.8 g, 0.04 mol) in hydrobromic acid (5.8 ml) and stirred at 50° C. for 10-15 minutes. The reaction mixture is cooled to room temperature, then poured into ice-cold water and extracted with ethyl acetate (3×300 ml). The organic extracts are washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to yield 4-bromo-4′-chloro-3-methylbiphenyl (11.5 g).

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to between −5° C. and 0° C.
  2. temperaturethe reaction mixture is maintained at between −5° C. and 0° C. for 30-40 minutes
  3. stirringstirred at 50° C. for 10-15 minutes
  4. temperatureThe reaction mixture is cooled to room temperature
  5. additionpoured into ice-cold water
  6. extractionextracted with ethyl acetate (3×300 ml)
  7. washThe organic extracts are washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-bfcdb1d490d340b3aa4b2dd6faffe227
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895761B2

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