Water → 3-Trifluoromethyl-4-vinylaniline

HRID 2070033ノート

反応式

HRID 2070033 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].O.[C:14](N)(C)(C)[CH3:15].FC(OB([O-])[O-])=C(F)F.[K+].[K+]>C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:10][C:9]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:2]=1[CH:14]=[CH2:15])[NH2:6]

参加物

7

反応物 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 86620274Potassium trifluorovinylborate

生成物 1

HCID 231551723-Trifluoromethyl-4-vinylaniline収率 79%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 3776Isopropanol溶媒

反応条件

温度
80 °C

実験手順

4-Bromo-3-(trifluoromethyl)aniline (4.0 g, 16.7 mmol) was dissolved in isopropanol (20 mL), water (10 mL), and t-butylamine (5 mL). To the solution, potassium(trifluoro)vinylborate (4.0 g, 29.9 mmol), PdCl2(dppf)2.2-dichloromethane complex (300 mg, 0.37 mmol) were added. The resulting mixture was stirred under argon atmosphere at 80° C. for 20 hours and then concentrated. The residue was partitioned between water and ethyl acetate, and the organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting product was purified by silica-gel column chromatography (n-hexane:ethyl acetate=6:1) to give 3-trifluoromethyl-4-vinylaniline (2.475 g, 79%) as a light-yellow oil.

後処理

  1. addition2-dichloromethane complex (300 mg, 0.37 mmol) were added
  2. concentrationconcentrated
  3. customThe residue was partitioned between water and ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting product was purified by silica-gel column chromatography (n-hexane:ethyl acetate=6:1)

出典と根拠

ORDレコード
ord-6eb1ebd3178146babfd787f8b81ef64f
出典データセット
uspto-grants-2012_10
特許番号
US08299252B2

反応ノート

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