2-Bromobiphenyl → 9-(2-Biphenylyl)-2,7-dibromo-9-fluorenol

HRID 635125

Reaktionsgleichung

Reaktionsgleichung von HRID 635125
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:15][C:16]1[CH:28]=[CH:27][C:26]2[C:25]3[C:20](=[CH:21][C:22]([Br:29])=[CH:23][CH:24]=3)[C:19](=[O:30])[C:18]=2[CH:17]=1>C(OCC)C>[C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:19]1([OH:30])[C:18]2[CH:17]=[C:16]([Br:15])[CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][C:22]([Br:29])=[CH:23][CH:24]=2

Komponenten

5

Edukt 3

HCID 163292-BromobiphenylHCID 2599222,7-Dibromo-9-fluorenoneHCID 5462224Magnesium

Produkt 1

HCID 220160479-(2-Biphenylyl)-2,7-dibromo-9-fluorenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A Grignard reagent prepared from 0.72 g (30 mmol) of magnesium turnings and 5.1 ml (30 mmol) of 2-bromobiphenyl in 15 ml of diethyl ether was added dropwise to a boiling suspension of 10.0 g (29.6 mmol) of 2,7-dibromo-9-fluorenone in 100 ml of dry diethyl ether with stirring (in an ultrasound bath) over the course of 2 h. When addition is complete, the mixture is boiled for a further 3 hours. After cooling overnight, the precipitate which had formed was filtered off with suction and washed with cold ether. The magnesium complex which had been filtered off with suction was hydrolyzed in a solution of 15 g of ammonium chloride in 250 ml of iced water. After 1 h, the 9-(2-biphenylyl)-2,7-dibromo-9-fluorenol which formed was filtered off with suction, washed with water and was sucked dry. For the ring-closure reaction, the dried fluorenol was boiled for 6 hours in 100 ml of glacial acetic acid, after the additon of 3 drops of conc. HCl. The mixture was left to crystallize overnight, and the product which formed was filtered off with suction and washed with glacial acetic acid and water.

Aufarbeitung

  1. additionWhen addition
  2. waitthe mixture is boiled for a further 3 hours
  3. temperatureAfter cooling overnight
  4. customthe precipitate which had formed
  5. filtrationwas filtered off with suction
  6. washwashed with cold ether
  7. filtrationThe magnesium complex which had been filtered off with suction
  8. waitAfter 1 h

Quellen und Nachweise

ORD-Eintrag
ord-ba2eacacc3ea40b58dabd120001cb371
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187224B1

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