Trifluoromethanesulfonic anhydride → 4-Cyano-2-methoxyphenyl trifluoromethanesulfonate

HRID 2090188Notes

Reaction equation

HRID 2090188 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[O:25][CH3:26]>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=1[O:25][CH3:26])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 781354-Hydroxy-3-methoxybenzonitrile

Product 1

HCID 166592584-Cyano-2-methoxyphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

24 ml (141 mmol) of trifluoromethanesulfonic anhydride are slowly added dropwise to a solution of 20 g (134 mmol) of 4-hydroxy-3-methoxybenzonitrile in pyridine (80 ml), keeping the reaction temperature below 25° C. with the aid of an ice bath. The suspension is then stirred at RT for 1 h. Ice-water (400 ml) is added, and the suspension is stirred further until room temperature is reached. It is then filtered, the solid is dissolved in ethyl acetate, and the solution is washed with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. 37.13 g (92% of theory) of the title compound are obtained as a white solid.

Workup

  1. customthe reaction temperature below 25° C.
  2. stirringthe suspension is stirred further until room temperature
  3. filtrationIt is then filtered
  4. dissolutionthe solid is dissolved in ethyl acetate
  5. washthe solution is washed with saturated sodium chloride solution
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-62041c40230642bc8561a5d8c9f1a30b
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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