Trifluoromethanesulfonic anhydride → 5-Cyano-2-formylphenyl trifluoromethanesulfonate

HRID 2090192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090192
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 593496385-Cyano-2-formylphenyl trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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-diisopropyl-ethylamine 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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c0017c77fa0046c78fd03ea32842b394
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436180B2

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