1H,1H,5H-OCTAFLUOROPENTYL P-TOLUENESULFONATE synthesis

Yield:2264-00-8 93%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 17 h;

Steps:

1b 2,2,3,3,4,4,5,5-Octafluoropentyl 4-methylbenzenesulfonate (19f):

Et₃N (70 mL, 500 mmol, 2.0 eq.) was added to a solution of 2,2,3,3,4,4,5,5- octafluoropentan-1-ol (34.8 mL, 250 mmol, 1.0 eq.) in DCM (200 mL) at room temperature. The mixture was cooled to 0 C using an ice/water bath and TsCl (47.7 g, 250 mmol, 1.0 eq.) was added portionwise over a period of 30 minutes. The mixture was stirred for 30 minutes at 0 C and then 16 h at room temperature. The reaction mixture was cooled to 0 C and acidified using 10% aqueous HCl (100 mL) under vigorous stirring. After 15 minutes, the mixture was transferred to an extraction funnel, additional water (100 mL) was added and the organic layer was separated. The aqueous phase was extracted with three portions of DCM (3 x 100 mL) and the combined organic fractions were dried with Na₂SO₄, filtrated and the solvent evaporated under reduced pressure. The obtained crude product (112.5 g, 93% yield) was used in the next step without further purification.

References:

WO2022/8283,2022,A1 Location in patent:Page/Page column 17-18; 19-20