2,6-Lutidine → 2-Fluoro-2-methylpropyl trifluoromethanesulfonate

HRID 1749017Notes

Reaction equation

HRID 1749017 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.N1C(C)=CC=CC=1C.[F:24][C:25]([CH3:29])([CH3:28])[CH2:26]O>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][CH2:26][C:25]([F:24])([CH3:29])[CH3:28])(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 111261792-Fluoro-2-methylpropan-1-ol

Product 1

HCID 121655342-Fluoro-2-methylpropyl trifluoromethanesulfonateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (12.06 ml, 71.24 mmol), followed by 2,6-lutidine (11.42 ml, 81.42 mmol) were added to a solution of 2-fluoro-2-methylpropan-1-ol (6.25 g, 67.85 mmol) in DCM (146 ml) at −10° C. The reaction was stirred for 1 hr. then washed with 2N HCl (2×100 ml) and saturated NaHCO3 solution (2×100 ml). The organic phase was then cried over Na2SO4 and concentrated to give 2-fluoro-2-methylpropyl trifluoromethanesulfonate (12.89 g, 85%) as a red oil.

Workup

  1. washthen washed with 2N HCl (2×100 ml) and saturated NaHCO3 solution (2×100 ml)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-09596fbf63b24ffa99e3afd778733aa7
Source dataset
uspto-grants-2015_10
Patent number
US09155727B2

Reaction notes

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