ChemicalBook CAS DataBase List Trifluoromethanesulfonic acid difluoromethyl ester

Trifluoromethanesulfonic acid difluoromethyl ester synthesis

5synthesis methods

Product Name:Trifluoromethanesulfonic acid difluoromethyl ester
CAS Number:1885-46-7
Molecular formula:C2HF5O3S
Molecular Weight:200.08

1493-13-6 Synthesis

1493-13-6
622 suppliers
$12.00/5g

81290-20-2 Synthesis

81290-20-2
408 suppliers
$13.00/1g

Trifluoromethanesulfonic acid difluoromethyl ester

1885-46-7
55 suppliers
$16.00/100mg

Yield:1885-46-7 74%

Reaction Conditions:

Stage #1:trifluorormethanesulfonic acid with titanium tetrachloride for 0.0833333 h;Inert atmosphere;Schlenk technique;
Stage #2:(trifluoromethyl)trimethylsilane at -20 - 20; for 1 h;Inert atmosphere;Schlenk technique;

Steps:

4.1.7.1 Preparation of difluoromethyl triflate
Triflic acid (1.2 eq., 8.45g, 5mL, 56.3mmol) was introduced into a Schlenk's vessel using a gas-tight syringe and was then carefully treated with TiCl₄ (1.17%, 0.104g, 0.06mL, 0.547mmol) under an inert atmosphere and vigorous stirring. After 5min, the homogeneous solution was evacuated at 13mbar over 10min until gas evolution ceased. The mixture was cooled to-20°C and Ruppert's reagent (6.65g, 7mL, 46.8mmol) was very carefully added via syringe, the mixture was stirred for 5minat-20°C, and then very slowly rose to room temperature by placing a water bath. The mixture was stirred 1h more. Volatile materials were distilled off in vacuo (130mbar) and trapped in N₂ trap. The volatile material was recovered from the N₂ trap after slow temperature rise under argon, to afford 9.82g of colourless liquid difluoromethyl trifluoromethanesulfonate (6.97g, 34.8mmol, 74%). ¹H NMR (CDCl₃, 400MHz): δ=6.64 (t, J_H-F=60Hz, 1H, -CHF₂) ppm.

References:

Naret, Timothée;Bignon, Jérôme;Bernadat, Guillaume;Benchekroun, Mohamed;Levaique, Helene;Lenoir, Christine;Dubois, Joelle;Pruvost, Alain;Saller, François;Borgel, Delphine;Manoury, Boris;Leblais, Veronique;Darrigrand, Romain;Apcher, Sébastien;Brion, Jean-Daniel;Schmitt, Etienne;Leroux, Frédéric R.;Alami, Mouad;Hamze, Abdallah [European Journal of Medicinal Chemistry,2018,vol. 143,p. 473 - 490]

FullText

1717-59-5 Synthesis