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

HRID 464027

Reaktionsgleichung

Reaktionsgleichung von HRID 464027
[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]>CCOCC.[Cu]Br>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:14][C:13]#[CH:12])=[CH:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 7806p-BromochlorobenzeneHCID 1394031-Methoxypropa-1,2-dieneHCID 5462224Magnesium

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

Place 59 g (2.43 mole) of magnesium turnings into a four-neck flask equipped with mechanical stirrer under N2 atmosphere. Add 500 ml of anhydrous ether and then add a solution of 465 g (2.43 mole) of 1-bromo-4-chlorobenzene in 1000 ml of anhydrous ether dropwise while stirring. Stir one hour after the completion of addition. Transfer and add this Grignard reagent to a solution of 170 g (2.43 mole) of 1-methoxy-1,2-propanediene and 69 g of copper (I) bromide in 300 ml of anhydrous ether with cooling. Stir for another ten minutes after the completion of addition. Add saturated aqueous solution of ammonium hydroxide and decant ether solution. Wash the solid residue with ether (3×50 ml). Wash the combined ether solutions with 1N HCl, saturated aqueous sodium bicarbonate, and with H2O. Dry over magnesium sulfate, evaporate, and distill in vacuo to yield the title compound, b.p. 99°-105° C. (15 mmHg).

Aufarbeitung

  1. stirringStir one hour
  2. additionafter the completion of addition
  3. temperaturewith cooling
  4. stirringStir for another ten minutes
  5. additionafter the completion of addition
  6. customAdd saturated aqueous solution of ammonium hydroxide and decant ether solution
  7. washWash the solid residue with ether (3×50 ml)
  8. washWash the combined ether solutions with 1N HCl, saturated aqueous sodium bicarbonate
  9. dry with materialDry over magnesium sulfate
  10. customevaporate
  11. distillationdistill in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9fb62b8a79e4438f98e0f3f914fc6c04
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04545995

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