Diethyl Ether → HCID 89851679、化合物

HRID 1771433ノート

反応式

HRID 1771433 の反応式
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

参加物

9

反応物 4

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

生成物 1

HCID 89851679HCID 89851679、化合物

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8003Pentane溶媒HCID 81998Tributylvinyltin溶媒

反応条件

温度
40 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-acad2e6cefae4a1bb3ca2925ff9b7393
出典データセット
uspto-grants-2016_02
特許番号
US09249127B2

反応ノート

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