Trifluoromethanesulfonic anhydride → (2-Cyano-5-methoxyphenyl)trifluoromethanesulphonate

HRID 1614772Notes

Reaction equation

HRID 1614772 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].[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1O)#[N:17]>N1C=CC=CC=1>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])#[N:17]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 114236802-Hydroxy-4-methoxybenzonitrile

Product 1

HCID 19771853(2-Cyano-5-methoxyphenyl)trifluoromethanesulphonateYield 81.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulphonic anhydride (2.06 g) was added dropwise to a solution of 2-cyano-5-methoxyphenol (1.0 g) in dry pyridine (20 ml) at 0° C. under an atmosphere of argon. Volatile material was removed by evaporation and the residue was dissolved in ethyl acetate (30 ml). The solution was washed with water (60 ml) and saturated sodium chloride solution (30 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with ethyl acetate/hexane (1:3 v/v), to give (2-cyano-5-methoxyphenyl)trifluoromethanesulphonate (1.53 g) as an oil; NMR (CDCl3): 3.9(s,3H), 6.95(d,1H), 7.0(d,1H), 7.7(d,1H).

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  3. washThe solution was washed with water (60 ml) and saturated sodium chloride solution (30 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:3 v/v)

Sources & evidence

ORD record
ord-d1a5297e4c98418ca424bb25d9846b8c
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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