1,3-Dibromobenzene → 1-(3-Bromo-phenyl)-3-hydroxy-3-methyl-butan-2-one

HRID 861000

Reaktionsgleichung

Reaktionsgleichung von HRID 861000
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[OH:9][C:10]([CH3:15])([CH3:14])[C:11](=[O:13])[CH3:12].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[Na])(C)(C)C>C1COCC1.[NH4+].[Cl-].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]>[Br:8][C:4]1[CH:3]=[C:2]([CH2:12][C:11](=[O:13])[C:10]([OH:9])([CH3:15])[CH3:14])[CH:7]=[CH:6][CH:5]=1

Komponenten

8

Edukt 4

HCID 79271,3-DibromobenzeneHCID 82613-Hydroxy-3-methyl-2-butanoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 178418730sodium 2-methylpropan-2-olate

Produkt 1

HCID 693741511-(3-Bromo-phenyl)-3-hydroxy-3-methyl-butan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1,3-dibromobenzene (1.0 eq.), 3-hydroxy-3-methyl-butan-2-one (1.0 eq.), Pd2(dba)3 (0.02 eq.), xantphos (0.04 eq.) and t-BuONa (1.1 eq.) in THF (0.15M) was stirred at 60° C. for 2 h, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 7:3) afforded the title compound as an oil.

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-341157c5382d465799e3515ab65a2bd0
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153968B2

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