Dimethylformamide → 4-(Pentafluoroethyl)benzonitrile

HRID 19770

반응식

HRID 19770 반응식
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:19])([F:18])[C:12]([F:17])([F:16])C([O-])=O.[Na+].CN(C=O)C>[Cu]I.C1(C)C=CC=CC=1>[F:16][C:12]([F:17])([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:11]([F:19])([F:18])[F:10]

참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 764674-IodobenzonitrileHCID 2733305Sodium pentafluoropropionate

생성물 1

HCID 147741854-(Pentafluoroethyl)benzonitrile수율 52.3%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매2회

반응 조건

온도
160 °C

실험 절차

A mixture of 4-iodobenzonitrile (10.0 g, 43.7 mmol), sodium pentafluoroproprionate (15.4 g, 82.9 mmol), and copper(I) iodide (16.6 g, 87.3 mmol), DMF (160 mL), and toluene (60 mL) was heated at 160° C. for 16 h, allowing most of the toluene to distil off. After cooling, ethyl acetate (200 mL) was added, and the mixture was filtered through diatomaceous earth, and the filtrate was partitioned between ethyl acetate/heptane and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (5.05 g 52%). Yellow oil, MS (EI) 221.1 (M+).

후처리

  1. customto distil off
  2. temperatureAfter cooling
  3. additionethyl acetate (200 mL) was added
  4. filtrationthe mixture was filtered through diatomaceous earth
  5. customthe filtrate was partitioned between ethyl acetate/heptane and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

출처 및 근거

ORD 기록
ord-ffd08d2350414257bcb2b75fcce9e152
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745477B2

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