N-bromobutanimide → 2-(Bromomethyl)-3-chloro-1,1'-biphenyl

HRID 485547

Reaktionsgleichung

Reaktionsgleichung von HRID 485547
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 46018323-Chloro-2-methylbiphenyl

Produkt 1

HCID 133207002-(Bromomethyl)-3-chloro-1,1'-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A stirred solution of 3-chloro-2-methyl-[1,1'-biphenyl] (13.5 g, 0.067 mole) and N-bromosuccinimide (11.8 g, 0.067 mole) in 125 ml of carbon tetrachloride was irradiated and heated to reflux for 61/2 hours with a 250 watt brooder lamp. The light/heat source was turned off and the reaction mixture stirred at room temperature for approximately 64 hours. The reaction mixture was again irradiated and heated for two hours with the brooder lamp. The mixture was cooled, a solid precipitate filtered off, and the filter cake washed with two 50 ml portions of carbon tetrachloride. The filtrate was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated under reduced pressure to give 2-bromomethyl-3-chloro-[1,1'-biphenyl] as an oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 61/2 hours with a 250 watt brooder lamp
  3. customThe reaction mixture was again irradiated
  4. temperatureheated for two hours with the brooder lamp
  5. temperatureThe mixture was cooled
  6. filtrationa solid precipitate filtered off
  7. washthe filter cake washed with two 50 ml portions of carbon tetrachloride
  8. washThe filtrate was washed with saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b7a18eff385e4042a9dc0af6f0add935
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536591

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