Dimethyl Disulfide → HCID 55268435, compound

Temperature

-78 °C

To a stirred solution of 4-bromo-2-fluoroanisole (5.0 g, 24.4 mmol) in THF (100 mL) was added n-butyllithium (23 mL, 1.6M in hexanes, 36.8 mmol) at −78° C. After stirring at −78° C. for 1 h, dimethyl disulfide (11 mL, 12.2 mmol) was added and the reaction was then allowed to warm to room temperature slowly. After stirring at room temperature for 12 h, the reaction was quenched with saturated aqueous ammonium chloride solution. The organic phase was separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo. The residue was used directly in next step.

1. temperatureto warm to room temperature slowly
2. stirringAfter stirring at room temperature for 12 h
3. customthe reaction was quenched with saturated aqueous ammonium chloride solution
4. customThe organic phase was separated
5. extractionthe aqueous phase was extracted with two portions of ethyl acetate
6. washThe combined organic layers were washed with brine
7. concentrationconcentrated in vacuo

ORD record

ord-e8fe7469d0c14aab854c65d97b168497

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687492B2