Azobisisobutyronitrile → Methyl 3,5-dibromo-4-(bromomethyl)benzoate

HRID 1157245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157245
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[Br:14]NC(=O)CCC(N)=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([Br:1])[C:11]([CH2:12][Br:14])=[C:10]([Br:13])[CH:9]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 624016Methyl 3,5-dibromo-4-methylbenzoateHCID 9834204N-Bromosuccinamide

Produkt 1

HCID 22647948Methyl 3,5-dibromo-4-(bromomethyl)benzoateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A solution of methyl 3,5-dibromo-4-methylbenzoate (5 g, 16.24 mmol) in carbon tetrachloride (50 mL) was treated with N-bromosuccinamide (3.6 g, 20.23 mmol) and 2,2′-azobisisobutyronitrile (0.56 g, 3.410 mmol). The reaction mixture was heated to reflux for 24 h. The reaction was cooled to room temperature and concentrated under vacuum. The resulting mixture was absorbed onto silica and was purified by flash chromatography using silica gel eluted with 3:1 hexanes:ethyl acetate. The desired fractions were collected and concentrated under vacuum to afford a solid which was dried under high vacuum to afford 3,5-dibromo-4-bromomethyl-benzoic acid methyl ester (57) (6.22 g, 99%) as a yellow solid; LRMS for C9H7Br3O2 (M+Na) m/z=407. MW=386.8669, Exact Mass=383.7996

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated under vacuum
  4. customThe resulting mixture was absorbed onto silica
  5. customwas purified by flash chromatography
  6. washeluted with 3:1 hexanes
  7. customThe desired fractions were collected
  8. concentrationconcentrated under vacuum
  9. customto afford a solid which
  10. customwas dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0dfb1a7fd51343198b75f7ecfb4bf8c2
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807674B2

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