Water → 2-(Benzyloxy)-1-bromo-3,5-difluorobenzene

HRID 451700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451700
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[OH:10].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.[OH-].[K+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1COCC1>[CH2:17]([O:10][C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 27362902-Bromo-4,6-difluorophenol

Produkt 1

HCID 467393982-(Benzyloxy)-1-bromo-3,5-difluorobenzeneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
64 °C

Versuchsvorschrift

2-Bromo-4,6-difluoro-phenol (10 g, 48 mmol), Bu4NBr (0.24 g, 0.72 mol) and BnBr (8.22 g, 48 mmol) was mixed in THF (100 mL). 50% KOH (13.46 g, 240 mmol) was added to the mixture, heated to 64° C. and stirred for 2 h. Water was added to the mixture, the aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product 2-(benzyloxy)-1-bromo-3,5-difluorobenzene (13.7 g, 96%), which was used immediately without purification.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dcd84c1e2a634e4498fcffdf2a6188a7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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