Water → (3-Bromophenyl)trimethylsilane

Participants

Reaction Conditions

Reaction Steps

26.49 ml (42.39 mmol) of a solution of BuLi (1.5M/hexane) are added dropwise, with stirring, over 30 min, to a solution of 10 g (42.39 mmol) of 1,3-dibromobenzene in 80 ml of anhydrous Et2O, cooled to −78° C. and maintained under a nitrogen atmosphere. After stirring for a further 30 min at −78° C., 5.96 ml (46.63 mmol) of TMSCl are introduced dropwise into the reaction mixture. The stirring is maintained at this temperature for 90 min and the reaction mixture is subsequently hydrolysed by adding 15 ml of water. The product is extracted with ethyl acetate (3×50 ml). The combined organic phases are washed with a saturated aqueous solution of NaCl (2×25 ml), dried over Na2SO4, filtered and evaporated under reduced pressure. The reaction crude is purified by silica gel column chromatography, elution being carried out with heptane, so as to isolate 9.3 g of the expected 1-bromo-3-trimethylsilylbenzene, in the form of a colourless oil.

Provenance & Evidence