Trifluoromethanesulfonic anhydride → 5-Cyano-2-formylphenyl trifluoromethanesulfonate

HRID 2170950Notes

Reaction equation

HRID 2170950 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].[CH:16]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=1O)=[O:17].C(N(CC)C(C)C)(C)C>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:25]1[CH:24]=[C:21]([C:22]#[N:23])[CH:20]=[CH:19][C:18]=1[CH:16]=[O:17])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 128136484-Formyl-3-hydroxybenzonitrile

Product 1

HCID 593496385-Cyano-2-formylphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.4 ml (14.27 mmol) of trifluoromethanesulfonic anhydride are added dropwise to a solution of 2 g (13.59 mmol) of 4-formyl-3-hydroxybenzonitrile and 2.5 ml (14.27 mmol) of N,N-diisopropylethylamine in 37 ml of anhydrous dichloromethane at 0° C. under an argon atmosphere. The reaction mixture is stirred at RT for 1 h, then diluted with 70 ml of dichloromethane and washed successively with 1 M hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic solution is dried over magnesium sulfate and concentrated. The residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1). 2.36 g (62% of theory) of the title compound are obtained as a white solid.

Workup

  1. washwashed successively with 1 M hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution
  2. dry with materialThe organic solution is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:1)

Sources & evidence

ORD record
ord-0e219f00444a4ff183595d10e04e045d
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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