N-bromobutanimide → HCID 14770215, Verbindung

HRID 1165643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165643
[CH3:1][C:2]1[C:3]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[CH:14][C:6]1[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=1[CH:4]=2.[Br:19]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[C:3]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[CH:14][C:6]1[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=1[CH:4]=2

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 14770214HCID 14770214, Verbindung

Produkt 1

HCID 14770215HCID 14770215, VerbindungAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a RB flask was added 7-methyl-benzo[b]naphtho[2,3-d]furan (Cambridge Chemicals, Inc., 16.0 g, 0.07 mol), N-bromosuccinimide (Alsrich 12.8 g, 0.072 mol, recrystallized from H2O and dried under high vacuum overnight), a catalytic amount of benzoyl peroxide (0.01 g) and CCl4 (1 L). The mixture was refluxed for 2.5 h, cooled and filtered to remove the succinimide formed in the reaction. The solvent was then removed from the reaction mixture by rotary evaporation. The crude product was purified by flush chromatograhy on SiO2 using PhCH3 as the eluting solvent. The appropriate fractions were combined and the solvent once again removed by rotary evaporation to give 22.0 g of product. The material (which was one spot by TLC and pure by NMR) was used without further purification.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove the succinimide
  5. customformed in the reaction
  6. customThe solvent was then removed from the reaction mixture by rotary evaporation
  7. customThe crude product was purified
  8. customby flush chromatograhy on SiO2
  9. customthe solvent once again removed by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-be20690c68c84be4b0ecc4812f199e64
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910218

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