1-(2-Bromo-4-fluorophenyl)ethan-1-one → 2-Bromo-1-(2-bromo-4-fluorophenyl)ethanone

HRID 1717682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717682
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Br-:12].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>O1CCCC1>[Br:12][CH2:10][C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])=[O:11]

Komponenten

4

Edukt 2

HCID 27363041-(2-Bromo-4-fluorophenyl)ethan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

Produkt 1

HCID 218649482-Bromo-1-(2-bromo-4-fluorophenyl)ethanoneAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 1-(2-Bromo-4-fluoro-phenyl)ethanone (2.5 g, 11.52 mmol) in anhydrous tetrahydrofuran (53 mL) under argon was added phenyltrimethylammonium tribromide (4.33 g, 11.52 mmol, 1.0 eq) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h, concentrated, and re-dissolved in ethyl acetate. The organic layer was washed with water (2×150 mL) and brine (1×100 mL), dried (MgSO4), filtered, and evaporated in vacuo. Purification using MPLC chromatography (Biotage) gave 2.14 g (63%) of 2-bromo-1-(2-bromo-4-fluoro-phenyl)-ethanone as a clear oil. 1H-NMR (CD2Cl2) δ 7.57 (dd, J=9.6 Hz, 1H), 7.44 (dd, J=8, 2 Hz, 1H), 7.21 (m, 7.21-7.14, 1H), 4.51 (s, 2H); TLC Rf=0.38, 15% ethyl acetate-hexanes.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionre-dissolved in ethyl acetate
  3. washThe organic layer was washed with water (2×150 mL) and brine (1×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-09b2551de25048afad84390ed8512051
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803956B2

Notizen zur Reaktion

Wird geladen…