Diethyl Ether → HCID 89851679, 화합물

HRID 1771433노트

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HRID 1771433 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([F:12])([F:11])[F:10].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C([O:28][CH2:29][CH3:30])C.[F-].[K+]>C1(C)C=CC=CC=1.C([Sn](CCCC)(CCCC)C=C)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCCCC>[F:10][C:9]([F:12])([F:11])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:30]1[CH2:29][O:28]1

참가 물질

9

반응물 4

HCID 3283Diethyl EtherHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 457904731-Bromo-2-(2,2,2-trifluoroethyl)benzene

생성물 1

HCID 89851679HCID 89851679, 화합물

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8003Pentane용매HCID 81998Tributylvinyltin용매

반응 조건

온도
40 °C

실험 절차

Bromo-2-(2,2,2-trifluoroethyl)benzene (0.5 g) was dissolved in degassed toluene and tributyl(vinyl)tin (0.67 mL), Pd2(dba)3 (0.096 g) and tri-tert-butylphosphine (0.25 mL, 1M solution) were added. Reaction mixture was heated to 40° C. After 4 hours heating was stopped and 1:1 solution of diethyl ether and pentane (10 ml) was added, followed by potassium fluoride (1.0 g). Mixture was stirred for 30 minutes after which it was filtered through a pad of silicagel and the filtrate was concentrated gently at 500 mbar vacuum. The evaporation residue was purified by column chromatography (diethyl ether-pentane) and fractions containing the product were concentrated by house vacuum distillation. The evaporation residue (0.389 g) containing toluene and the desired styrene product was dissolved in dichloromethane (12 mL) and 3-chloroperoxybenzoic acid (0.70 g) was added.

후처리

  1. customReaction mixture
  2. temperatureAfter 4 hours heating
  3. filtrationwas filtered through a pad of silicagel
  4. concentrationthe filtrate was concentrated gently at 500 mbar vacuum
  5. customThe evaporation residue was purified by column chromatography (diethyl ether-pentane) and fractions
  6. additioncontaining the product
  7. concentrationwere concentrated by house vacuum distillation
  8. additionThe evaporation residue (0.389 g) containing toluene
  9. dissolutionthe desired styrene product was dissolved in dichloromethane (12 mL)
  10. addition3-chloroperoxybenzoic acid (0.70 g) was added

출처 및 근거

ORD 기록
ord-acad2e6cefae4a1bb3ca2925ff9b7393
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249127B2

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