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

HRID 2255513노트

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HRID 2255513 반응식
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]

참가 물질

5

반응물 2

HCID 9636IodopentafluoroethaneHCID 792252-Iodo-5-nitrotoluene

생성물 1

HCID 105871021-Pentafluoroethyl-2-methyl-4-nitro-benzene

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매

반응 조건

온도
-60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-454f1c5c24394990a67e51e1e5c024c0
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05240960

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