Potassium Hydroxide → 2-(Benzyloxy)-3-fluorophenol

HRID 39016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39016
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:17]1CCOCC1.[OH-].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:1]([O:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 532169822-(Benzyloxy)-1-chloro-3-fluorobenzene

Produkt 1

HCID 107751752-(Benzyloxy)-3-fluorophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-(benzyloxy)-1-chloro-3-fluorobenzene (3 g, 12.71 mmol), dioxane (6 ml), KOH (0.78 g, 14 mmol), water (6 ml), Tris(dibenzylideneacetone)dipalladium (0.12 g, 0.13 mmol) and 2-di-tertbutylphosphine-2,4,6-triisopropylbiphenyl (0.22 g, 0.51 mmol) was flushed with N2 and heated under microwave radiation at 120° C. for 7 min. HCl (1 N) was added and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness. Flash column chromatography (isooctane/EtOAc) yielded the title compound (1.86 g). MS m/z (rel. intensity, 70 eV) 218 (M+, 4), 92 (8), 91 (bp), 65 (13), 51 (9).

Aufarbeitung

  1. customwas flushed with N2
  2. additionHCl (1 N) was added
  3. extractionthe solution was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9ab18781cc814d62921fc9a44e38d60c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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