Methanesulfonyl chloride → 3,3,3-Trifluoropropyl methanesulfonate

To a solution of 3,3,3-trifluoropropan-1-ol (500 mg, 4.38 mmol) in DCM (10 mL) was added TEA (1.22 mL, 8.77 mmol) followed by dropwise addition of methanesulfonyl chloride (0.51 mL, 6.58 mmol) at 0° C. The resulting mixture was stirred at room temperature for 2 h. The reaction was diluted with DCM and the organic phase washed with brine, dried and concentrated to give crude product which was purified via silica gel chromatography eluting with petroleum ether/ethyl acetate (5:1) to give 3,3,3-trifluoropropyl methanesulfonate (490 mg, 58.2% yield) as light yellow oil. TLC (petroleum ether/ethyl acetate=3:1), Rf=0.6.

1. washthe organic phase washed with brine
2. customdried
3. concentrationconcentrated
4. customto give crude product which
5. customwas purified via silica gel chromatography
6. washeluting with petroleum ether/ethyl acetate (5:1)

ORD record

ord-a1aed81d00694da09b02c99e85dac7fa

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359359B2