Dimethylformamide → 4-(Pentafluoroethyl)benzonitrile

HRID 19770

反応式

HRID 19770 の反応式
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]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 764674-IodobenzonitrileHCID 2733305Sodium pentafluoropropionate

生成物 1

HCID 147741854-(Pentafluoroethyl)benzonitrile収率 52.3%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒2 回

反応条件

温度
160 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-ffd08d2350414257bcb2b75fcce9e152
出典データセット
uspto-grants-2010_06
特許番号
US07745477B2

関連ノート

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