Benzene, 1-bromo-2-(trifluoromethyl)- → Stannane, tributyl[2-(trifluoromethyl)phenyl]-

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Reaction Steps

To a solution of 10.0 g of 2-bromotrifluoromethylbenzene under nitrogen in 100 ml of tetrahydrofuran while cooling in a dry ice-acetone bath is added dropwise 30.6 ml of a 1.6M solution of butyl lithium via syringe. Stirring is continued for 1 hour. To the reaction mixture is added dropwise 15.9 g of tributyltin chloride in 30 ml of tetrahydrofuran. Stirred ? additional hours. The reaction mixture is quenched with 20 ml of water and after stirring for 20 minutes, extracted with chloroform (3×100 ml). The organic layer is filtered through diatomaceous earth and the filtrate washed with saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and evaporated in vacuo to give 16.8 g of the desired product. MS 379.1

Provenance & Evidence