3-Phenoxybenzyl chloride → HCID 13194582, Verbindung

HRID 354698

Reaktionsgleichung

Reaktionsgleichung von HRID 354698
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:16].[K+]>[Br-].C([P+](CCCC)(CCCC)CCCCCCCCCCCCCCCC)CCC.O>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 932913-Phenoxybenzyl chlorideHCID 522689Potassium Fluoride

Produkt 1

HCID 13194582HCID 13194582, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84716Hexadecyltributylphosphonium bromideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Phenoxybenzyl chloride (4.37 g), potassium fluoride (5.8 g), tri-n-butylhexadecylphosphonium bromide (1.2 g) and water (10 ml) were stirred for a period of 8 hours in a pressure bottle heated at a temperature of 130° C. The oil was separated and the aqueous phase was diluted with water and extracted with ethylene dichloride. The oil and ethylene dichloride extract were combined and the phosphonium salt was removed by chromatography over silica gel (15 g). The eluate was concentrated and distilled to give 3-phenoxybenzyl fluoride (1.96 g; 49%) b.p. 92°-95° C. at 0.3 mm Hg. (The product was stabilized by the addition of a small amount of anhydrous calcium carbonate to prevent acid catalysed polymerization).

Aufarbeitung

  1. customThe oil was separated
  2. additionthe aqueous phase was diluted with water
  3. extractionextracted with ethylene dichloride
  4. extractionThe oil and ethylene dichloride extract
  5. customthe phosphonium salt was removed by chromatography over silica gel (15 g)
  6. concentrationThe eluate was concentrated
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-cdcd3a4ab5264453a0fe4d4efc250155
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04376784

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