반응 #11277

반응 방정식

2-bromofluorene

DMSO

NaOH

n-octylbromide

→

2-bromo-9,9-dioctylfluorene

수율 155.4%

용매

water ether

hexane

반응 조건

후처리

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 2 hours
3. 3
   workup.ADDITIONTo the reaction mixture was added
4. 4
   기타the organic layer separated
5. 5
   세척was washed successively with brine
6. 6
   건조Drying over magnesium sulfate and evaporation of the solvent
7. 7
   기타gave an oil
8. 8
   기타Purification by column chromatography (silica gel

실험 절차

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 benzyltriethylammonium 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 hours. To the reaction mixture was added 500 mL of a 1:1 mixture of water/ether, and the organic layer separated and was 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 as a pale oil.

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