Dimethyl Disulfide → (5-Chloro-2-fluoro-3-methoxyphenyl)(methyl)sulfane

Temperature

-78 °C

To a mixture of 4-chloro-1-fluoro-2-methoxybenzene (2.0 g) and THF (dry) (100 mL) was added sec-butyllithium (1.04 mol/L cyclohexane solution, 23.95 mL) dropwise over a period of 45 min at −78° C. After stirring at −78° C. for 30 min, to the mixture was added dimethyl disulfide (2.468 mL) at the same temperature. The mixture was stirred at −78° C. for 1.5 h under argon atmosphere. The mixture was quenched with saturated aqueous NH4Cl at −78° C. and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give a solid. The solid was washed with hexane to give the title compound (1.77 g).

1. stirringThe mixture was stirred at −78° C. for 1.5 h under argon atmosphere
2. customThe mixture was quenched with saturated aqueous NH4Cl at −78° C.
3. extractionextracted with EtOAc
4. washThe organic layer was washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
8. customto give a solid
9. washThe solid was washed with hexane

ORD record

ord-d7efb83c9b1946c4873bbc058b23d792

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2