Iodine → p-Chloroprenylbenzene

HRID 1903592

Reaktionsgleichung

Reaktionsgleichung von HRID 1903592
[Mg].II.C(Br)C.Br[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.[CH2:15](Cl)[CH:16]=[C:17]([CH3:19])[CH3:18].[Cl-].[NH4+]>O1CCCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:9][CH:10]=1

Komponenten

8

Edukt 6

HCID 807Iodine2×HCID 6332Ethyl BromideHCID 7806p-BromochlorobenzeneHCID 104291-Chloro-3-methyl-2-buteneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Produkt 1

HCID 316460p-ChloroprenylbenzeneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Under nitrogen atmosphere, 55.1 g of magnesium turnings, 800 ml of tetrahydrofuran, and about 0.1 g of several pieces of iodine were put in a flask. With stirring, 2 ml of ethyl bromide was added, whereupon coloration by iodine disappeared. Then, a solution of 361.7 g of p-bromochlorobenzene in 2 liters of tetrahydrofuran was added dropwise at such a speed that the reaction temperature was maintained at 25° C. to 30° C. After the addition, the mixture was further stirred for 1 hour, and cooled to about 20° C. A solution of 256.8 g of prenyl chloride in 800 ml of tetrahydrofuran was added dropwise at 15° C. to 20° C. over the course of about 4 hours. After the addition, the mixture was left to stand overnight at room temperature. Two liters of a 10% by weight aqueous solution of ammonium chloride were added, and the mixture was separated into an organic layer and an aqueous layer. The aqueous layer was extracted with 300 ml of diethyl ether. The diethyl ether layer was combined with the organic layer previously separated, and washed with water, dried, concentrated, and distilled to give 218.3 g (yield 64.0%) of p-chloroprenylbenzene.

Aufarbeitung

  1. temperaturewas maintained at 25° C. to 30° C
  2. additionAfter the addition
  3. stirringthe mixture was further stirred for 1 hour
  4. additionAfter the addition
  5. waitthe mixture was left
  6. customthe mixture was separated into an organic layer
  7. extractionThe aqueous layer was extracted with 300 ml of diethyl ether
  8. custompreviously separated
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated
  12. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-e845d51c3bf74f8088a6672306956ca5
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436939

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