Dimethyl Sulfoxide → 2-Bromo-9,9-di-n-octylfluorene

HRID 1180526

Reaktionsgleichung

Reaktionsgleichung von HRID 1180526
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CS(C)=O.[OH-].[Na+].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCCCCC.O.CCOCC>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH2:11][CH3:10])([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81401-BromooctaneHCID 143362-Bromo-9H-fluoreneHCID 14798Sodium Hydroxide

Produkt 1

HCID 129646932-Bromo-9,9-di-n-octylfluoreneAusbeute 155,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 8058HexaneLösungsmittelHCID 21584184Diethylether waterLösungsmittel

Versuchsvorschrift

A 3L flask fitted with a mechanical stirrer was charged with 2-bromofluorene (45 g, 183.6 mmole) and 150 mL DMSO. Under a N2 atmosphere was added 80 mL of a 50% aqueous NaOH solution and 2.72 g of benzyl triethylammonium chloride (2.72 g, 11.98 mmole). This was stirred for 2 h at RT. With vigorous mechanical stirring, n-octylbromide (84.96 g, 440 mmole) was added via a dropping funnel (exotherm). Stirring was continued for 2 h. To the reaction mixture was added 500 mL of a 1:1 mixture of water/ether and the organic layer separated and washed successively with brine and then water. Drying over magnesium sulfate and evaporation of the solvent gave an oil. Purification by column chromatography (silica gel; hexane as the mobile phase) gave 67 g (78% yield) of 2-bromo-9,9-dioctylfluorene (9) as a pale oil.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 2 h
  3. additionTo the reaction mixture was added
  4. customthe organic layer separated
  5. washwashed successively with brine
  6. dry with materialDrying over magnesium sulfate and evaporation of the solvent
  7. customgave an oil
  8. customPurification by column chromatography (silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f2a860accfa34c6bbea30a9467ba8c90
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282275B2

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