p-Bromochlorobenzene → 1-Chloro-4-(2-propyn-1-yl)benzene

HRID 1380344

Reaktionsgleichung

Reaktionsgleichung von HRID 1380344
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.CO[CH:12]=[C:13]=[CH2:14].[Cl-].[NH4+]>CCOCC.OC(C1C=CC(NS(C)(=O)=O)=CC=1)CN1C=CN=C1>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:14][C:13]#[CH:12])=[CH:4][CH:5]=1

Komponenten

7

Edukt 4

HCID 7806p-Bromochlorobenzene2×HCID 25517Ammonium ChlorideHCID 1394031-Methoxypropa-1,2-dieneHCID 5462224Magnesium

Produkt 1

HCID 136602551-Chloro-4-(2-propyn-1-yl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 13763390N-[4-(1-Hydroxy-2-(1H-imidazol-1-yl)ethyl]phenyl]methanesulfonamideLösungsmittel

Versuchsvorschrift

In a flask containing 59 g (2.43 mole) magnesium turnings in 500 ml anhydrous ether under an atmosphere of nitrogen, and slowly a solution of 465 g (2.43 mole) of 4-bromochlorobenzene in 1 liter 4 anhydrous ether. With caution, once the Grignard has started maintain slow reflux until all 4-bromochlorobenzene has been added. Stir an additional hour and then add this Grignard (maintain slow reflux) to a suspension of 170 g (2.43 mole) methoxyallene and 69 g of cuprous bromide in 300 ml anhydrous ether under N2. When addition is complete, stir another 10 minutes and then add saturated ammonium chloride. Decant off the ether solution wash the solid residue with ether (3×50 ml). Combine the ether extracts and wash with 1N HCl, saturated aqueous sodium bicarbonate, water and dry over magnesium sulfate. Evaporate off the ether and distill the residue in vacuo to obtain the title compound (99-105 mmHg).

Aufarbeitung

  1. temperatureWith caution, once the Grignard has started maintain slow
  2. additionhas been added
  3. additionadd
  4. temperaturethis Grignard (maintain slow reflux)
  5. additionWhen addition
  6. stirringstir another 10 minutes
  7. customDecant off the ether solution
  8. washwash the solid residue with ether (3×50 ml)
  9. washCombine the ether extracts and wash with 1N HCl, saturated aqueous sodium bicarbonate, water
  10. dry with materialdry over magnesium sulfate
  11. customEvaporate off the ether
  12. distillationdistill the residue in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4aa74c6da4be459394e1d919e2ca96a0
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04581370

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