Iodoethane → (3-Bromo-4-fluorophenyl)(ethyl)sulfane

Temperature

0 °C

A mixture of 3-bromo-4-fluorobenzenethiol (3.89 g, 18.79 mmol) and sodium hydroxide (3.95 mL, 19.73 mmol) in MeOH was stirred at 0° C. for 10 minutes. To this solution was added iodoethane (1.803 mL, 22.54 mmol). The reaction mixture was stirred at ambient temperature for 6 hours. The solvent was removed, and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with addition ethyl acetate three times. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the title compound (4.35 g, 18.50 mmol, 98% yield). It was used directly for the next reaction.

1. stirringThe reaction mixture was stirred at ambient temperature for 6 hours
2. customThe solvent was removed
3. customthe residue was partitioned between water and ethyl acetate
4. extractionThe aqueous layer was extracted with addition ethyl acetate three times
5. washThe combined organic layers were washed with saturated aqueous sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-20ca365096ac468786d1ce827bda3d91

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296741B2