N-bromobutanimide → 5-Bromo-7-bromomethylbenzofuran

HRID 1584771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1584771
[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.[W].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][Br:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1

Komponenten

7

Edukt 2

HCID 67184N-bromobutanimideHCID 111066535-Bromo-7-methylbenzofuran

Produkt 1

HCID 196085405-Bromo-7-bromomethylbenzofuranAusbeute 113,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 7187Benzoyl PeroxideKatalysator2×HCID 23964TungstenKatalysatorHCID 5943Carbon TetrachlorideLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-7-methyl-benzofuran (1.01 g), N-bromosuccinimide (1.04 g) and benzoyl peroxide (58 mg) in carbon tetrachloride (10 ml) was heated at reflux for 4 h under a 250 W tungsten lamp. A further portion of benzoyl peroxide (58 mg) was added and heating and irradiation continued for a total of 9 h. The reaction mixture was allowed to cool, diluted with chloroform (30 ml) and washed with 2N sodium hydroxide (40 ml) and then brine (40 ml). The organic phase was dried, filtered and the filtrate evaporated in vacuo to give the title compound as a brown oil (1.57 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureheating
  3. customirradiation
  4. customcontinued for a total of 9 h
  5. temperatureto cool
  6. washwashed with 2N sodium hydroxide (40 ml)
  7. customThe organic phase was dried
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cfb06f118b2846c5987f3d1a1c9fc2da
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05935972

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