Nitrogen → 2-Fluoro-3-trifluoromethyl-4-vinylaniline

HRID 2044193

反応式

HRID 2044193 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[C:3]=1[C:10]([F:13])([F:12])[F:11].[CH2:14](C([Sn](Cl)(Cl)Cl)=C(CCCC)CCCC)[CH2:15]CC.N#N>CN(C=O)C>[F:9][C:4]1[C:3]([C:10]([F:13])([F:12])[F:11])=[C:2]([CH:14]=[CH2:15])[CH:8]=[CH:7][C:5]=1[NH2:6]

参加物

5

反応物 3

HCID 947NitrogenHCID 536697144-Bromo-2-fluoro-3-(trifluoromethyl)anilineHCID 86633508Tributylvinyltin chloride

生成物 1

HCID 688215442-Fluoro-3-trifluoromethyl-4-vinylaniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

4-Bromo-2-fluoro-3-trifluoromethylaniline described above (5.0 g, 19.4 mmol) and tributylvinyltin chloride (7.1 g, 20.4 mmol) are added to anhydrous DMF (100 mL). The solution is degassed with N2, palladium tetrakistriphenylphosphine (1.5 g, 1.3 mmol) is added, and the reaction is heated at 120° C. for 18 hours. After cooling, the reaction mixture is partitioned between Et2O and saturated aqueous NaCl. The separated ether layer is washed with fresh saturated aqueous NaCl (2×), dried with Na2SO4, and concentrated under reduced pressure. The residue is purified by flash chromatography eluting with 5, then 10, then 20% EtOAc in hexanes to give the desired product, 2-fluoro-3-trifluoromethyl-4-vinylaniline.

後処理

  1. additionis added
  2. temperatureAfter cooling
  3. customthe reaction mixture is partitioned between Et2O and saturated aqueous NaCl
  4. washThe separated ether layer is washed with fresh saturated aqueous NaCl (2×)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography
  8. washeluting with 5

出典と根拠

ORDレコード
ord-04f31d4162d7439da67565543f0659d3
出典データセット
uspto-grants-2013_11
特許番号
US08586782B2

関連ノート

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