Trifluoromethanesulfonic anhydride → 3,3,4,4,4-Pentafluorobutyl trifluoromethanesulphonate

Temperature

56 °C

198.49 g (703.51 mmol) of trifluoromethanesulphonic anhydride were initially charged under argon. The reaction flask was immersed into an oil bath at 70° C. and heated to internal temperature 56° C. 88.2 ml (738.68 mmol) of 3,3,4,4,4-pentafluorobutanol were added dropwise to the reaction mixture within 35 min and the mixture was stirred at bath temperature 70-73° C. and internal temperature 69° C. for two hours. The reaction mixture was concentrated on a rotary evaporator and the residue was taken up in 1500 ml of dichloromethane. The residue was washed once with 300 ml of cold water, once with 300 ml of cold saturated aqueous sodium hydrogencarbonate solution and once with 300 ml of cold water. The organic phase was dried with magnesium sulphate, filtered and concentrated. This gave 192.86 g (92.6% of theory) of the target compound.

1. customThe reaction flask was immersed into an oil bath at 70° C.
2. concentrationThe reaction mixture was concentrated on a rotary evaporator
3. washThe residue was washed once with 300 ml of cold water, once with 300 ml of cold saturated aqueous sodium hydrogencarbonate solution and once with 300 ml of cold water
4. dry with materialThe organic phase was dried with magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-28c581e2c1944ea78ee5316ca6aea9db

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422285B2