Dimethyl Disulfide → (2-Fluoro-3-methoxy-5-methylphenyl)(methyl)sulfane

Temperature

-78 °C

To a mixture of 1-fluoro-2-methoxy-4-methylbenzene (1.0 g) and THF (dry) (60 mL) was added sec-butyllithium (1.04 mol/L cyclohexane solution, 13.72 mL) dropwise over a period of 20 min at −78° C. After stirring at −78° C. for 20 min, to the mixture was added dimethyl disulfide (1.41 mL) at the same temperature. The mixture was stirred at −78° C. under argon atmosphere for 1 h. The mixture was quenched with saturated aqueous NH4Cl at −78° C. and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.34 g).

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

ORD record

ord-59bc9a1c62cc4837a7ce4f8213a325b2

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238639B2