Reaction #1960503

Reaction equation

7,8-difluoro-3-trimethylsilanylnaphthalen-2-ol

bromoethane

potassium carbonate

→

(3-ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane

Solvents

ethyl methyl ketone

Conditions

Workup

1. 1
   FiltrationThe batch is filtered
2. 2
   Washthe residue is washed with ethyl methyl ketone
3. 3
   ConcentrationThe filtrate is concentrated
4. 4
   WashThe solution is washed with water and sat. sodium chloride soln
5. 5
   Otherand dried
6. 6
   Otherafter removal of the solvent
7. 7
   Otheris purified by column chromatography (SiO2, toluene:ethyl acetate=9:1)

Procedure

54.7 g (about 0.12 mol) of 7,8-difluoro-3-trimethylsilanylnaphthalen-2-ol are stirred at 80° C. for 19 h together with 19.5 ml (0.26 mol) of bromoethane and 34.5 g (0.25 mol) of potassium carbonate in 400 ml of ethyl methyl ketone. The batch is filtered, and the residue is washed with ethyl methyl ketone. The filtrate is concentrated, and the residue is taken up in MTBE. The solution is washed with water and sat. sodium chloride soln. and dried using sodium sulfate. The residue remaining after removal of the solvent is purified by column chromatography (SiO2, toluene:ethyl acetate=9:1), giving (3-ethoxy-5,6-difluoronaphthalen-2-yl)trimethylsilane as a dark-brown solid.

Source