Iodopentafluoroethane → 1-Pentafluoroethyl-2-methyl-4-nitro-benzene

HRID 1770014ノート

反応式

HRID 1770014 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[F:12][C:13](I)([F:18])[C:14]([F:17])([F:16])[F:15]>CN(C)C=O.[Cu]>[F:12][C:13]([F:18])([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11])[C:14]([F:17])([F:16])[F:15]

参加物

5

反応物 2

HCID 9636IodopentafluoroethaneHCID 792252-Iodo-5-nitrotoluene

生成物 1

HCID 105871021-Pentafluoroethyl-2-methyl-4-nitro-benzene収率 65.5%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-60 °C

実験手順

A mixture of 2.36 g of 1-iodo-2-methyl-4-nitro-benzene and 2.2 g of powdered copper (Org. Synthesis Coll., Vol. II (1948), page 445 washed with water, acetone and dried under reduced pressure) in 10 ml of dimethylformamide under nitrogen in a sealed vessel was cooled to -60° C. and 11.5 g of pentafluoroethyl iodide were added. The mixture was stirred at 160° C. at a pressure of 3.5 bars for 16 hours and then cooled in ice and returned to room temperature. The mixture was poured into ice and was extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica (eluant--pentane containing 2 to 3% of dichloromethane) to obtain 1.5 g of 1-pentafluoroethyl-2-methyl-4-nitro-benzene which was hydrogenated in the presence of palladized active carbon to obtain the desired product.

後処理

  1. temperaturecooled in ice
  2. customreturned to room temperature
  3. additionThe mixture was poured into ice
  4. extractionwas extracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated to dryness under reduced pressure
  8. customThe residue was chromatographed over silica (eluant--pentane containing 2 to 3% of dichloromethane)

出典と根拠

ORDレコード
ord-0d88e706671745d28d20f8a5438cfdea
出典データセット
uspto-grants-1995_01
特許番号
US05384423

反応ノート

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