Benzoyl chloride → 2-Bromobenzophenone

HRID 131059

Reaktionsgleichung

Reaktionsgleichung von HRID 131059
[Li+].[Cl-].Br[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Br:10].C([Cu])#N.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Br:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:21]

Komponenten

6

Edukt 4

HCID 7412Benzoyl chlorideHCID 114141,2-DibromobenzeneHCID 433294Lithium ChlorideHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 27355342-Bromobenzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with i-PrMgCl.LiCl (1 mL, 1.05 M in THF, 1.05 mmole), the reaction mixture was cooled to −15° C. and 1,2-dibromobenzene (235.9 mg, 1 mmole) was then added dropwise. The Br/Mg-exchange was complete after 1.5 h (checked by GC analysis of reaction aliquots, conversion more than 98%) and solution of CuCN.2LiCl (0.1 mL, 1.0 M in THF, 0.1 mmole) was added. After stirring for 10 min at −15° C. benzoyl chloride (140.6 mg, 1 mmole) was added. The reaction mixture was stirred for 1 h at −15° C. and was then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3 was added. The aqueous phase was extracted with ether (3×4 mL) and the organic fractions were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (dichloromethane) yielding the ketone (2ka) as a white cristals (219.3 mg, 84%). 1H-NMR (CDCl3, 200 MHz): δ=7.86-7.78 (m, 2H); 7.68-7.56 (m, 2H); 7.52-7.30 (m, 5H).

Aufarbeitung

  1. customA dry
  2. customargon flushed 10 mL flask
  3. customequipped with a magnetic stirrer
  4. additiona septum, was charged with i-PrMgCl
  5. additionwas added
  6. customwas then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3
  7. additionwas added
  8. extractionThe aqueous phase was extracted with ether (3×4 mL)
  9. washthe organic fractions were washed with brine (5 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe crude residue was purified by flash chromatography (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6175b2d29c1a4eea9104d15720b7fd30
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384580B2

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