Water → 3-Trifluoromethyl-4-vinylaniline

HRID 2070033노트

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HRID 2070033 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 231551723-Trifluoromethyl-4-vinylaniline수율 79%

시약·촉매·용매 2

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

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6eb1ebd3178146babfd787f8b81ef64f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299252B2

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