Diiodomethane → HCID 57812583, compound

A 50 mL round-bottomed flask was charged with DCM (1 mL) at −30° C. under nitrogen with stirring. 1 M of diethyl zinc in hexane (1 mL) was added dropwise to the flask followed by the addition of diiodomethane (520 mg, 2.0 mmol). A solution of 1-(2-chloro-3,6-difluorophenyl)-prop-2-en-1-ol (50 mg, 0.2 mmol) in DCM was added to the reaction mixture at −20° C. with stirring. The reaction mixture was allowed to warm to rt and stirred for an additional 1 h. The reaction mixture was quenched with sat. aq. NH4Cl solution (15 mL) and extracted with DCM (20 mL). The organic layer was washed with brine (15 mL), dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure to yield a yellow oil. The material was purified by silica gel chromatography using Hexane/EtOAc (80:20) as eluent to give the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=0.39-0.48 (m, 1H), 0.48-0.60 (m, 2H), 0.67-0.76 (m, 1H), 1.55-1.63 (m, 1H), 2.48 (dd, J=8.1, 3.5 Hz, 1H), 4.46 (t, J=8.6 Hz, 1H), 6.97-7.10 (m, 2H).

1. stirringwith stirring
2. stirringstirred for an additional 1 h
3. customThe reaction mixture was quenched with sat. aq. NH4Cl solution (15 mL)
4. extractionextracted with DCM (20 mL)
5. washThe organic layer was washed with brine (15 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customThe solvent was evaporated under reduced pressure
9. customto yield a yellow oil
10. customThe material was purified by silica gel chromatography

ORD record

ord-fbe0ad1e35964fb4abc95011a66a6ecf

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2