Reaction #1960502

Reaction equation

2,3-difluorophenylacetyl chloride

aluminium(III) chloride

hydrochloric acid

trimethylsilylacetylene

→

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

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   OtherThe organic phase is separated off
2. 2
   Extractionthe aqueous phase is extracted with ethyl acetate
3. 3
   WashThe combined organic phases are washed successively with sat. sodium hydrogencarbonate soln
4. 4
   OtherThe solution is dried
5. 5
   Otherevaporated to dryness
6. 6
   OtherThe residue is purified by column chromatography (SiO2, n-heptane:ethyl acetate=9:1)

Procedure

A solution of 50.0 g (0.26 mol) of 2,3-difluorophenylacetyl chloride in 100 ml of dichloromethane is slowly added to a suspension of 71.5 g (0.53 mol) of aluminium(III) chloride in 300 ml of dichloromethane at −20° C. After 30 min at this temperature, trimethylsilylacetylene is metered in, and the mixture is stirred for 30 min. The batch is added to ice-water and acidified using hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed successively with sat. sodium hydrogencarbonate soln. and sat. sodium chloride soln. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:ethyl acetate=9:1), giving 7,8-difluoro-3-trimethylsilanylnaphthalen-2-ol as a brown oil.

Source