Tributyltin Chloride → (5-Chlorothien-2-yl)tributyl tin

Temperature

-80 °C

A stirred solution of 5.1 mL (0.046 mole) of 2-bromo-5-chlorothiophene in 200 mL of tetrahydrofuran was cooled to -85°C., and 19.7 mL (0.049 mole) of n-butyllithium (0.049 mole-2.5M in hexanes) was added dropwise during a 15 minute period. The reaction mixture temperature was maintained at -85° C. to -80° C. throughout the addition. Upon completion of addition, the reaction mixture temperature was maintained at about -80° C. for one hour. After this time, a solution of 12.5 mL (0.046 mole) of tributyltin chloride in 50 mL of tetrahydrofuran was added to the cold reaction mixture during a 10 minute period. Upon completion of addition, the reaction mixture was stirred at -80° C. for one hour, then it was allowed to warm gradually to ambient temperature. The reaction was quenched with an aqueous solution saturated with ammonium chloride, and then the reaction mixture was extracted with three 150 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 18.4 grams of (5-chlorothien-2-yl)tributyl tin. The NMR spectrum was consistent with the proposed structure.

1. temperatureThe reaction mixture temperature was maintained at -85° C. to -80° C. throughout the addition
2. additionUpon completion of addition
3. additionUpon completion of addition
4. temperatureto warm gradually to ambient temperature
5. customThe reaction was quenched with an aqueous solution saturated with ammonium chloride
6. extractionthe reaction mixture was extracted with three 150 mL portions of diethyl ether
7. dry with materialThe combined extracts were dried with magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-07d659d7c7a74ac8b44face641843d4d

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05874579