3,3,3-trifluoropropyl methansulfonate synthesis

Yield:911116-16-0 83%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 3 h;

Steps:

24.1 Step-1:
3,3,3-Trifluoropropyl methanesulfonate (46)


To a solution of 3,3,3-trifluoropropan-1-ol [2240-88-2] (5.0 g, 43.8 mmol) in CH₂Cl₂ (10 mL) was added TEA (12.3 mL, 87.7 mmol) followed by the dropwise addition of methanesulfonyl chloride (5 mL, 65.8 mmol) at 0° C.
The resulting mixture was stirred at room temperature for 3 h.
The reaction mixture was diluted with CH₂C₂ and the organic phase was washed with brine, dried over Na₂SO₄, filtered and concentrated to give the crude product that was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate (30%) to give 3,3,3-trifluoropropyl methanesulfonate [911116-16-0] (46) (7.0 g, 83% yield) as light yellow oil. C₄H₇F₃O₃S: ¹H NMR (400 MHz, CDCl₃): 4.43 (t, J=5.6 Hz, 2H), 3.05 (s, 3H), 2.66-2.55 (m, 2H).

References:

US2021/155652,2021,A1 Location in patent:Paragraph 0361-0363