Oxalyl chloride → [2-(Trifluoromethyl)phenyl]methanesulfonyl chloride

To a suspension of (2-trifluoromethylphenyl)methanesulfonic acid (20.3 g, 84 mmol) in THF (1.9 L) and DMF (5.0 mL) at −20° C. was added oxalyl chloride (44.7 mL, 0.5 mol) slowly dropwise over 1 hr. The bath temperature was maintained below 0° C. for 4 h, at which point the reaction was evaporated to a volume of ˜250 mL and diluted with 500 mL of ethyl acetate. This solution was washed with brine in a separatory funnel and dried over magnesium sulfate. The solution was then evaporated to a brown oil. This oil was taken up in 500 mL of pet ether (30-50°) and heated with a heat gun until the oil went into solution. The solution was then placed into a dry-ice acetone bath to cool resulting in formation of a white crystalline material. This material was collected via filtration and dried to afford 19 g (85%) of (2-trifluoromethylphenyl)methanesulfonyl chloride as a white solid.

1. temperatureThe bath temperature was maintained below 0° C. for 4 h, at which
2. customwas evaporated to a volume of ˜250 mL
3. additiondiluted with 500 mL of ethyl acetate
4. washThis solution was washed with brine in a separatory funnel
5. dry with materialdried over magnesium sulfate
6. customThe solution was then evaporated to a brown oil
7. customwas taken up in 500 mL of pet ether (30-50°)
8. temperatureheated with a heat gun until the oil
9. customThe solution was then placed into a dry-ice acetone bath
10. temperatureto cool
11. customresulting in formation of a white crystalline material
12. filtrationThis material was collected via filtration
13. customdried

ORD record

ord-cd94becf0cef4daa810dc654ef725589

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557135B2