Benzoyl Peroxide → 2,7-Dibromophenanthrene

HRID 2038951

Reaktionsgleichung

Reaktionsgleichung von HRID 2038951
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C([O-])(=O)C.[K+]>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH:6]=[CH:5][C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 517044Potassium AcetateHCID 28250532,7-Dibromo-9,10-dihydrophenanthrene

Produkt 1

HCID 111750732,7-DibromophenanthreneAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The mixture of 2,7-dibromo-9,10-dihydro-phenanthrene (2.4 g, 7.1 mmol), NBS (1.4 g, 7.8 mmol), and benzoyl peroxide (0.2 g) in carbon tetrachloride (300 ml) was refluxed for 2 hours. Potassium acetate (3.6 g) and acetic acid (3.2 ml) were added, and the refluxing was continued for additional 2 hours. The mixture was cooled and diluted with EtOAc. The organic phase was washed with water, saturated sodium bicarbonate, and brine, and was dried with sodium sulfate. Concentration gave 2,7-dibromo-phenanthrene (2.3 g).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe mixture was cooled
  3. washThe organic phase was washed with water, saturated sodium bicarbonate, and brine
  4. dry with materialwas dried with sodium sulfate
  5. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-da618f64604440dd9b6799e0c623ce3a
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575118B2

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