Reaction #1447106

Reaction equation

boron trifluoride

KOH

diisopropylether

(3-bromo-5-iodo-2-methyl-phenyl)-(4-ethyl-phenyl)-methanone

triethylsilane

→

3-Bromo-5-(4-ethyl-benzyl)-1-iodo-4-methyl-benzene

Solvents

dichloromethane

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONare added
2. 2
   OtherThe organic phase is separated
3. 3
   Extractionthe aqueous phase is extracted three times with diisopropylether
4. 4
   WashThe combined organic phases are washed with 2 M potassium hydroxide solution and brine
5. 5
   Dryingdried (sodium sulphate)
6. 6
   OtherAfter the solvent is evaporated
7. 7
   Otherthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0->1:1)

Procedure

A solution of (3-bromo-5-iodo-2-methyl-phenyl)-(4-ethyl-phenyl)-methanone (4.2 g) and triethylsilane (4.7 mL) in dichloromethane (10 mL) and acetonitrile (28 mL) is cooled in an ice-bath. Then, boron trifluoride diethyletherate (1.4 mL) is added dropwise over 3 min. The solution is stirred for 14 h at ambient temperature, before an aqueous 25% solution of KOH and diisopropylether are added. The organic phase is separated and the aqueous phase is extracted three times with diisopropylether. The combined organic phases are washed with 2 M potassium hydroxide solution and brine and then dried (sodium sulphate). After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 1:0->1:1).

Source