Trifluoromethanesulfonic anhydride → 5-Cyano-2-formylphenyl trifluoromethanesulfonate

HRID 1951381ノート

反応式

HRID 1951381 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 593496385-Cyano-2-formylphenyl trifluoromethanesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-685dc25ddbbb47c49bee318c75049295
出典データセット
uspto-grants-2013_03
特許番号
US08404709B2

反応ノート

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