Dimethylformamide → 4-(Pentafluoroethyl)benzonitrile

HRID 19770

Reaction equation

HRID 19770 reaction equation
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]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 764674-IodobenzonitrileHCID 2733305Sodium pentafluoropropionate

Product 1

HCID 147741854-(Pentafluoroethyl)benzonitrileYield 52.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
160 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-ffd08d2350414257bcb2b75fcce9e152
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Linked notes

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