Azobisisobutyronitrile → 1-(Bromomethyl)-2-fluoro-4-iodobenzene

HRID 491939

Reaktionsgleichung

Reaktionsgleichung von HRID 491939
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>CC(C)=O>[Br:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1].[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH3:9]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 1234922-Fluoro-4-iodotoluene

Produkt 2

HCID 1234922-Fluoro-4-iodotolueneAusbeute 17 %HCID 222404061-(Bromomethyl)-2-fluoro-4-iodobenzeneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Part C. To a solution of 2-fluoro-4-iodo-1-methylbenzene (50 g, 210 mmol) in anhydrous acetone (490 mL) was added N-bromosuccinimide (42 g, 230 mmol) and 2,2′-azobisiso-butyronitrile (100 mg, 0.60 mmol). The resulting solution was heated to reflux and maintained under reflux conditions for 5 h. The reaction was then cooled, concentrated, and filtered. The filtrate was concentrated, and the resulting dark red residue was purified by flash column chromatography (10% ethyl acetate in hexanes) to afford a 4:1 mixture (58 g) of 1-(bromomethyl)-2-fluoro-4-iodobenzene (49 g, 73%) and 2-fluoro-4-iodo-1-methylbenzene (9 g, 17%) as a red solid. 1H NMR (product) (CDCl3) δ 7.40-7.49 (m, 2H), 7.13 (t, 1H), 4.45 (s, 2H).

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperaturemaintained under reflux conditions for 5 h
  4. temperatureThe reaction was then cooled
  5. concentrationconcentrated
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe resulting dark red residue was purified by flash column chromatography (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-aa1796a7c81e4d3a8a211aa8a8786998
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531535B2

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