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 minutesat -78° C., 19.5 g (97.8 mmol) of trimethyltin chloride dissolved in30 ml of tetrahydrofuran was added dropwise and the mixture stirred for 10 minutes at -78° C. before allowing to warm to room temperature. Thereaction 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. additionwas added dropwise
2. stirringthe mixture stirred for 10 minutes at -78° C.
3. customThereaction mixture was quenched with excess saturated sodium bicarbonate
4. extractionextracted with ethyl acetate (300 ml)
5. washThe extract was washed with saturated sodium bicarbonate and brine
6. dry with materialdried over magnesium sulfate
7. customevaporated in vacuo
8. customto give a crude yield of 20.2 g of the above product
9. customisolated as a oily semi-solid

ORD record

ord-d162b977bc5046e581412dae5e6a535b

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05491126