Ethanol → 3-Ethenyl-2,6-difluorobenzonitrile

HRID 2175835ノート

反応式

HRID 2175835 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([C:14]#[N:15])[C:8]=1[F:16])(=O)=O.[CH2:19](O)[CH3:20]>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].C(Cl)Cl>[CH:19]([C:7]1[C:8]([F:16])=[C:9]([C:10]([F:13])=[CH:11][CH:12]=1)[C:14]#[N:15])=[CH2:20]

参加物

4

反応物 2

HCID 702EthanolHCID 867270593-Cyano-2,4-difluorophenyl trifluoromethanesulfonate

生成物 1

HCID 867270603-Ethenyl-2,6-difluorobenzonitrile

試薬・触媒・溶媒 1

HCID 178418807HCID 178418807、化合物触媒

実験手順

3-Cyano-2,4-difluorophenyl trifluoromethanesulfonate (5.20 g, 18.1 mmol), potassium vinyl trifluoroborate (4.85 g, 36.2 mmol), PdCl2(dppf)-CH2Cl2 Adduct (0.662 g, 0.905 mmol), and TEA (5.05 mL, 36.2 mmol) were added to 75 mL of ethanol. The reaction mixture was degassed then heated at reflux for 4 h. LC-MS analysis confirmed product peak. The reaction mixture was diluted with ethyl acetate, washed twice with brine, dried, and evaporated to dryness. The crude material was then purified by MPLC chromatography through a 330 g Redi-sep column eluting with 10% EtOAc/Hexane solvent system to yield 3-ethenyl-2,6-difluorobenzonitrile.

後処理

  1. customThe reaction mixture was degassed
  2. temperaturethen heated
  3. temperatureat reflux for 4 h
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. washwashed twice with brine
  6. customdried
  7. customevaporated to dryness
  8. customThe crude material was then purified by MPLC chromatography through a 330 g Redi-sep column
  9. washeluting with 10% EtOAc/Hexane solvent system

出典と根拠

ORDレコード
ord-757af68304c14e249a9cf72079d3ce52
出典データセット
uspto-grants-2015_06
特許番号
US09062070B2

反応ノート

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