2-Fluoro-4-iodoaniline → 3,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

HRID 1161783ノート

反応式

HRID 1161783 の反応式
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:21]1[C:29]([F:30])=[C:28]([F:31])[C:27]([N+:32]([O-:34])=[O:33])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]>C1COCC1>[F:30][C:29]1[C:21]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:2]=2[F:1])=[C:22]([CH:26]=[C:27]([N+:32]([O-:34])=[O:33])[C:28]=1[F:31])[C:23]([OH:25])=[O:24]

参加物

5

反応物 3

HCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium Hexamethyldisilazide2 回HCID 158712412,3,4-Trifluoro-5-nitrobenzoic acid

生成物 1

HCID 210742923,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
-78 °C

実験手順

To a solution of 2-fluoro-4-iodoaniline (2.9 g, 11.8 mmoles) in 50 ml anhydrous THF at −60° C., 40 ml of a 1M solution of LHMDS in THF (40 mmoles) is added dropwise. In a separate flask, 2,3,4-trifluoro-5-nitrobenzoic acid (5 g, 22.6 mmoles), previously dissolved in THF (50 ml), is treated, at −60° C., with 25 ml of a 1M solution of LHMDS in THF (25 mmoles). Both solutions are stirred at −78° C. for 45 min and the second solution is transferred via cannula to the first reaction mixture. After completion of the addition the resulting mixture is stirred under argon at room temperature for 15 hours. The reaction mixture is quenched with water, then 1N HCl is added (pH=0-1) followed by brine (100 ml). The crude material is extracted with THF (3×100 ml), the organic layers are combined and dried (Na2SO4) and the solvent is removed to give the title compound.

後処理

  1. additionAfter completion of the addition the resulting mixture
  2. stirringis stirred under argon at room temperature for 15 hours
  3. customThe reaction mixture is quenched with water
  4. addition1N HCl is added (pH=0-1)
  5. extractionThe crude material is extracted with THF (3×100 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent is removed

出典と根拠

ORDレコード
ord-4b6e6ca4670347028204acb407a82697
出典データセット
uspto-grants-2010_10
特許番号
US07820664B2

反応ノート

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