4,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenyl → 3,9-Dibromo-5,7-dihydrodibenzo[c,e]oxepine

HRID 417413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417413
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[CH2:15]O)=[C:4]([CH2:17][OH:18])[CH:3]=1>P(=O)(O)(O)O.O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[CH2:17][O:18][CH2:15][C:9]=2[CH:10]=1

Komponenten

4

Edukt 1

HCID 113721754,4'-Dibromo-2,2'-bis-hydroxymethyl-biphenyl

Produkt 1

HCID 223161653,9-Dibromo-5,7-dihydrodibenzo[c,e]oxepineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1004Phosphoric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

The suspension of (4,4′-dibromo-2′-hydroxymethyl-biphenyl-2-yl)-methanol (460 mg) in phosphoric acid (25 ml) was heated at 160° C. for 4 hours. The mixture was cooled and diluted with water (100 ml), and was extracted with EtOAC. The organic phase was washed with water, saturated sodium bicarbonate, and brine, and was dried with sodium sulfate. Concentration yielded 3,9-dibromo-5,7-dihydro-dibenzo[c,e]oxepine (416 mg).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionwas extracted with EtOAC
  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-09a9616737694472875d4021eeae5b61
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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