Benzene, 1-bromo-3-(trifluoromethyl)- → Trimethyl[3-(trifluoromethyl)phenyl]stannane

To 20.0 g (88.9 mmol) of meta-bromobenzotrifluoride stirring in 200 ml of tetrahydrofuran at 78° C., 61.2 ml of 1.6M n-butyl lithium (97.9 mmol) in hexane was added dropwise. After stirring the reaction 10 minutes at -78° C., 19.5 g (97.8 mmol) of trimethyltin chloride dissolved in 30 ml of tetrahydrofuran was added dropwise and the mixture stirred for 10 minutes at -78° C. before allowing to warm to room temperature. The reaction mixture was quenched with excess saturated sodium bicarbonate and extracted with ethyl acetate (300 ml). The extract was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated in vacuo to give a crude yield of 20.2 g of the above product, isolated as a oily semi-solid. This aryl stannane was used directly as a crude material in the coupling reactions with heterocycles of Formula II.

1. customthe reaction 10 minutes at -78° C.
2. additionwas added dropwise
3. stirringthe mixture stirred for 10 minutes at -78° C.
4. customThe reaction mixture was quenched with excess saturated sodium bicarbonate
5. extractionextracted with ethyl acetate (300 ml)
6. washThe extract was washed with saturated sodium bicarbonate and brine
7. dry with materialdried over magnesium sulfate
8. customevaporated in vacuo
9. customto give a crude yield of 20.2 g of the above product
10. customisolated as a oily semi-solid

ORD record

ord-d6f2ab1b3cdb491b84d6a65b056448be

Source dataset

uspto-grants-1995_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05389600