2-Fluoro-4-iodoaniline → 4-Amino-3-fluorobenzonitrile

HRID 2423346Notes

Reaction equation

HRID 2423346 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[Cu][C:11]#[N:12].C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([C:11]#[N:12])=[CH:8][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 1856942-Fluoro-4-iodoanilineHCID 516892Sodium BicarbonateHCID 178418546HCID 178418546, compound

Product 1

HCID 27564314-Amino-3-fluorobenzonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 50 ml of two-neck round bottom flask was filled with argon gas, and the solution of 2-fluoro-4-iodoaniline (1 g, 5.219 mmol, 1 equiv.) in DMF was put into the flask. To the solution was added Copper (I) cyanide (453.4 mg, 5.063 mmol, 1.2 equiv.) and heated to reflux for 5 hours. After confirming the completion of the reaction with TLC, saturated sodium bicarbonate solution was added to the solution and stirred for 5 minutes. The resulting solution was extracted with methylenechloride, washed with water and brine, dried over Na2SO4, filtered and evaporated. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/1) to yield a pale yellow solid (461.6 mg).

Workup

  1. additionA 50 ml of two-neck round bottom flask was filled with argon gas
  2. temperatureheated
  3. temperatureto reflux for 5 hours
  4. additionwas added to the solution
  5. extractionThe resulting solution was extracted with methylenechloride
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-713af144e6084e4cad0adec1aaf48ff7
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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