Iodine → HCID 71224849, compound

Temperature

-78 °C

1-Fluoro-3-propylbenzene (30 g, 0217 mol) and dry tetrahydrofurane (300 ml) were placed in 1 L flask equipped with mechanical stirrer, nitrogen inlet and outlet, 250 ml pressure-equilibrated dropping funnel and thermometer. The mixture was cooled down to −78° C. in a dry ice/acetone bath and 1.3 mol/L sec-butyllithium solution (170 ml, 0.221 mol) was added dropwise and the reaction temperature was kept below −70° C. After addition of all butyllithium solution the mixture was stirred for 2 hours at −78° C. and iodine (55.12 g, 0.217 mol) in dry tetrahydrofurane was added dropwise. Cooling bath was removed and heating to room temperature was allowed. The tetrahydrofurane was evaporated using rotary evaporator and the oily substance was washed off in separation funnel with sodium sulfite solution. Organic phase was separated dried over magnesium sulfate and filtered. The product was distilled under reduced pressure 0.4 mmHg, collecting the fraction of the transparent liquid boiling at 60° C. 43 g of 2-fluoro-1-iodo-4-propylbenzene was obtained, 75% of theor. yield.

1. customequipped with mechanical stirrer, nitrogen inlet and outlet
2. customwas kept below −70° C
3. temperatureCooling bath
4. customwas removed
5. temperatureheating to room temperature
6. customThe tetrahydrofurane was evaporated
7. customevaporator
8. washthe oily substance was washed off in separation funnel with sodium sulfite solution
9. customOrganic phase was separated
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. distillationThe product was distilled under reduced pressure 0.4 mmHg
13. customcollecting the fraction of the transparent liquid boiling at 60° C

ORD record

ord-fca14424c7394e4db885d69be944da12

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08652353B2