Hydrochloric Acid → N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

HRID 603336

反応式

HRID 603336 の反応式
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH2:4].[CH2:12]([C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)[CH3:13].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Cl>O.C1(C)C=CC=CC=1>[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH:4][C:17]1[CH:18]=[CH:19][C:14]([CH2:12][CH3:13])=[CH:15][CH:16]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 127862,3,5,6-TetrafluoroanilineHCID 153131-Bromo-4-ethylbenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

生成物 1

HCID 21938675N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

A mixture of 2,3,5,6-tetrafluoroaniline (4.5 g, 27.3 mmol), 4-ethylbromobenzene (5.0 g, 27 mmol), toluene (50 ml), sodium tert-butoxide (4.67 g, 48 mmol), tri-tert-butylphosphin (217 mg, 1.07 mmol) and bis-dibenzylideneacetone-palladium(0) (260 mg, 0.45 mmol) is heated under nitrogen to 85° C. for 15.5 h. The mixture is cooled to room temperature and water (30 ml), concentrated hydrochloric acid (20 ml) and hyflo are added. After stirring for 45 minutes, the mixture is filtered and the organic phase is washed with water three times. The solvent is evaporated in vacuo and the residue is chromatographed on silica using hexane/toluene (9:1 to 3:1) affording N-(2′,3′,5′,6′-tetrafluorophenyl)-4-ethylanilin as a liquid.

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationthe mixture is filtered
  3. washthe organic phase is washed with water three times
  4. customThe solvent is evaporated in vacuo
  5. customthe residue is chromatographed on silica

出典と根拠

ORDレコード
ord-db7c28842a0549feb90e747c0c7962f1
出典データセット
uspto-grants-2011_03
特許番号
US07906677B2

関連ノート

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