4-Bromopyridine → 8-Bromo-10,11-dihydro-10-(4-pyridinyl)dibenz[b,f]oxepin-10-ol

HRID 1982158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982158
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C([Li])CCC.[Li]C1C=CN=CC=1.[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[O:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[CH2:27][C:26](=[O:35])[C:25]=2[CH:36]=1>CCOCC.CCCCCC>[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[O:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[CH2:27][C:26]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)([OH:35])[C:25]=2[CH:36]=1

Komponenten

7

Edukt 4

HCID 142684-BromopyridineHCID 122458788-bromodibenz[b,f]oxepin-10(11H)-oneHCID 178418339ButyllithiumHCID 178506752HCID 178506752, Verbindung

Produkt 1

HCID 136086128-Bromo-10,11-dihydro-10-(4-pyridinyl)dibenz[b,f]oxepin-10-olAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, a solution of 4-bromopyridine (16.6 g) in anhydrous ether (90 ml) previously cooled to -40°, was transferred slowly via a cannular to a stirred solution of n-butyl lithium in hexane (1.55M; 68 ml) cooled to -78°. The mixture was stirred at -78° for 20 minutes and the resulting 4-lithiopyridine was transferred to a chilled (-78°) stirred suspension of 8-bromodibenz[b,f]oxepin-10(11H)-one (15 g) in anhydrous ether (100 ml). The reaction was stirred at -78° for 30 minutes, then the cooling bath was removed and the mixture was treated with 100 ml of water and allowed to warm to room temperature. The solids were filtered off, washed with water and dried to give 5.0 g of 8-bromo-10,11-dihydro-10-(4-pyridinyl)dibenz[b,f]oxepin-10-ol. The mother liquor was worked up and a total of 9.4 grams of the starting ketone 8-bromodibenz[b,f]oxepin-10(11H)-one were recovered.

Aufarbeitung

  1. temperaturecooled to -78°
  2. temperaturea chilled (-78°)
  3. stirringstirred
  4. stirringThe reaction was stirred at -78° for 30 minutes
  5. customthe cooling bath was removed
  6. additionthe mixture was treated with 100 ml of water
  7. filtrationThe solids were filtered off
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8537de479302484e9b21610f229c08e7
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04595689

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