Dimethyl Sulfoxide → 2-(4-Fluorophenyl)-2-methylpropanal

Temperature

-60 °C

To a stirred solution of oxalyl chloride (2.81 ml) in dichoromethane (30 ml) at −60° C. was added dropwise a solution of dry dimethyl sulphoxide (4.84 ml) in dichloromethane (20 ml). The mixture was stirred for 15 min at −60° C. and then a solution of 2-(4-fluoro-phenyl)-2-methyl-propan-1-ol (4.59 g; CAS 703-10-6) in dichloromethane (20 ml) was added dropwise. The mixture was stirred at −60° C. for 2 hours and then triethylamine (18.9 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and diluted with water and with dichloromethane. The phases were separated and the organic phase was washed with water and then dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane/EtOAc gradient) to yield a colourless oil, (3.47 g, 77%).

1. stirringThe mixture was stirred at −60° C. for 2 hours
2. temperatureto warm to room temperature
3. customThe phases were separated
4. washthe organic phase was washed with water
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc gradient)
8. customto yield a colourless oil, (3.47 g, 77%)

ORD record

ord-8b9de261259b495498cc7cd25466f845

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729113B2