Reaction #9770

Reaction equation

4-bromo-trifluoromethoxybenzene

sodium carbonate

triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane

intermediate 116

triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane

→

title compound

triisopropyl({3-methyl-5-[4-(trifluoromethoxy)phenyl]thien-2-yl}methoxy)silane

Solvents

1,2-dimethoxyethane

water

Conditions

Workup

1. 1
   Temperatureat reflux for 2 hours
2. 2
   Otherpartitioned between water and ethyl acetate
3. 3
   OtherThe aqueous layer was separated
4. 4
   Extractionextracted with further ethyl acetate
5. 5
   Dryingdried over magnesium sulfate
6. 6
   OtherThe crude product was purified by Si SPE

Procedure

A mixture of triisopropyl{[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]methoxy}silane (intermediate 116, 0.40 g) in 1,2-dimethoxyethane (12 ml) and water (6 ml) was treated with 4-bromo-trifluoromethoxybenzene (0.26 g), sodium carbonate (0.26 g) and tetrakis(triphenylphosphine)palladium (0) (0.120 g). The reaction mixture was stirred at reflux for 2 hours and then partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with further ethyl acetate and then the organic solutions combined and dried over magnesium sulfate. The crude product was purified by Si SPE using dichloromethane as eluent to give the title compound as a yellow gum.

Source