Iodine → 1-Iodo-3,5-bis(trifluoromethyl)benzene

Under a nitrogen atmosphere, a stirred solution of 15.0 grams (0.051 mole) of 3,5-di(trifluoromethyl)phenyl bromide in 45 mL of dry tetrahydrofuran was cooled to below -80° C., and 20.5 mL (0.051 mole) of n-butyllithium (2.5M in hexanes) was added dropwise while maintaining the reaction mixture temperature below -80° C. Upon completion of addition, an additional 50 mL of tetrahydrofuran was added to promote stirring. The reaction mixture was then stirred at -80° C. for an additional one hour. After this time a solution of 13.0 grams (0.051 mole) of iodine in 30 mL of tetrahydrofuran was added dropwise while maintaining the reaction mixture temperature below -80° C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was then poured into 400 mL of water, and the mixture was extracted with one 200 mL portion of diethyl ether. The ether extract was washed with an aqueous solution of 10 % meta-sodium bisulfate. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 13.1 grams of 3,5-di(trifluoromethyl)phenyl iodide.

1. temperaturewhile maintaining the reaction mixture temperature below -80° C
2. additionUpon completion of addition
3. stirringThe reaction mixture was then stirred at -80° C. for an additional one hour
4. temperaturewhile maintaining the reaction mixture temperature below -80° C
5. additionUpon completion of addition
6. extractionthe mixture was extracted with one 200 mL portion of diethyl ether
7. extractionThe ether extract
8. washwas washed with an aqueous solution of 10 % meta-sodium bisulfate
9. dry with materialThe organic layer was dried with magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-5a2480f630744398add7585914fdd24e

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05536725