反応 #11277

反応方程式

2-bromofluorene

DMSO

NaOH

n-octylbromide

→

2-bromo-9,9-dioctylfluorene

収率 155.4%

溶媒

water ether

hexane

反応条件

後処理

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for 2 hours
3. 3
   workup.ADDITIONTo the reaction mixture was added
4. 4
   その他the organic layer separated
5. 5
   洗浄was washed successively with brine
6. 6
   乾燥Drying over magnesium sulfate and evaporation of the solvent
7. 7
   その他gave an oil
8. 8
   その他Purification by column chromatography (silica gel

実験手順

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.

出典