Water → HCID 59556994, compound

Temperature

-78 °C

A solution of diisopropylamine (6.06 mL) in THF (100 mL) was cooled to −78° C., n-butyllithium-hexane (24.9 mL, 1.6 mol/L) was added dropwise and, after the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr. Subsequently, a solution of 4-bromo-2-fluoro-1-iodobenzene (10.0 g) in THF (50 mL) was added dropwise, and the mixture was further stirred at −78° C. for 1 hr. Methyl iodide (2.90 mL) was added dropwise at −78° C. and the mixture was further stirred at −78° C. for 2 hr, and the mixture was warmed to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a brown oil (yield: 10.5 g, yield: 100%).

1. additionn-butyllithium-hexane (24.9 mL, 1.6 mol/L) was added dropwise
2. additionafter the completion of the dropwise addition
3. stirringthe mixture was further stirred at −78° C. for 1 hr
4. stirringthe mixture was further stirred at −78° C. for 2 hr
5. temperaturethe mixture was warmed to room temperature
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-718457ea321d4aeda5a05f47f218c4f5

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834051B2