1-Bromo-3-fluorobenzene → 1,2-Bis(3-fluorophenyl)ethane-1,2-dione

HRID 18710

Reaktionsgleichung

Reaktionsgleichung von HRID 18710
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[Br-].[Li+].[F:12][C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[CH:17][CH:18]=1.[C:21](Cl)(=[O:25])[C:22](Cl)=[O:23]>C1COCC1.[Cu]Br>[F:9][C:5]1[CH:4]=[C:3]([C:22]([C:21]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=2)=[O:25])=[O:23])[CH:8]=[CH:7][CH:6]=1

Komponenten

8

Edukt 5

HCID 140821-Bromo-3-fluorobenzeneHCID 65578Oxalyl chlorideHCID 82050Lithium BromideHCID 5462224MagnesiumHCID 178505773HCID 178505773, Verbindung

Produkt 1

HCID 225742141,2-Bis(3-fluorophenyl)ethane-1,2-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel4×

Reaktionsbedingungen

Temperatur
21 °C

Versuchsvorschrift

To anhydrous THF (80 mL) is added magnesium (2.9 g, 0.120 mol) and 1-bromo-3-fluorobenzene (12.76 g, 0.114 mol) in anhydrous THF (30 mL). The mixture is stirred at 21° C. for 1.5 h. To THF (60 mL) is added lithium bromide (13.22 g, 0.015 mol) and copper (I) bromide (10.9 g, 0.0762 mol) and the mixture is stirred at RT until homogenous, then cooled to 0° C. To this solution is added 3-fluorophenylmagnesium bromide solution followed by a solution of oxalyl chloride (2.76 mL, 0.0317 mol) in THF (20 mL). The solution is stirred at 0° C. for 15 min, then quenched by ammonium chloride solution, and extracted with EtOAc. The organic solution is dried (Na2SO4), filtered, and the filtrate rotary evaporated. The residue is purified by filtration through silica gel; elution with heptane and heptane:EtOAc (9:1) gives 0.70 g of the product 20.

Aufarbeitung

  1. stirringthe mixture is stirred at RT until homogenous,
  2. temperaturethen cooled to 0° C
  3. stirringThe solution is stirred at 0° C. for 15 min
  4. customquenched by ammonium chloride solution
  5. extractionextracted with EtOAc
  6. dry with materialThe organic solution is dried (Na2SO4)
  7. filtrationfiltered
  8. filtrationThe residue is purified by filtration through silica gel
  9. washelution with heptane and heptane:EtOAc (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-c0c1e0df18c94a9ca39c1c89c56dfe92
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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