N-bromobutanimide → Methyl 3-(bromomethyl)-2-benzofurancarboxylate

HRID 2221442

Reaktionsgleichung

Reaktionsgleichung von HRID 2221442
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:15][CH2:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 74953Methyl 3-methyl-2-benzofurancarboxylate

Produkt 1

HCID 100838Methyl 3-(bromomethyl)-2-benzofurancarboxylateAusbeute 108,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A solution of methyl 3-methylbenzofuran-2-carboxylate (1.0 g, 5.3 mmol), N-bromosuccinimide (0.95 g, 5.3 mmol) and 2,2′-azobisisobutyronitrile (87 mg, 0.53 mmol) was heated to reflux in CCl4 (40 ml) for 3 h, then cooled to room temperature and concentrated. The residue was dissolved in ethyl acetate (100 ml) and washed with water (100 ml). The organic layer was dried over magnesium sulfate and concentrated to provide crude methyl 3-bromomethylbenzofuran-2-carboxylate (1.55 g) as a yellowish solid, which was used in the next step without further purification.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed with water (100 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8cf3f5e8500348a69a4705b088f22356
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368572B2

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