Dimethylformamide → 2-((2-Fluorophenyl)amino)benzonitrile

HRID 2237487Notes

Reaction equation

HRID 2237487 reaction equation
F[NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[F:15][C:16]1C=[CH:22][CH:21]=[CH:20][C:17]=1C#N.[CH3:24][N:25]([CH:27]=O)C>O>[F:15][C:16]1[CH:17]=[CH:20][CH:21]=[CH:22][C:24]=1[NH:25][C:27]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[C:3]#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 678552-FluorobenzonitrileHCID 17888012FluoroanilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 286020842-((2-Fluorophenyl)amino)benzonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A solution of fluoroaniline (6.8 ml, 71 mmol) in DMF (100 ml) was treated with potassium tert-butoxide (12.7 g, 113 mmol) and then with 2-fluorobenzonitrile (7.5 ml, 71 mmol) that was slowly added to the stirring reaction with a syringe and stirred at 23° C. for 16 h. The reaction mixture was diluted with H2O (100 mL) and extracted with ethyl ether (3×50 mL), dried with (MgSO4), and evaporated. Flash chromatography (SiO2, 2-100% dichloromethane/heptane) provided 2-[(2-fluorophenyl)amino]benzonitrile (8.4 g 56%) as an orange solid:

Workup

  1. extractionextracted with ethyl ether (3×50 mL)
  2. dry with materialdried with (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-dc0a0bb4504540878dfbdc010d2baa8a
Source dataset
uspto-grants-2010_05
Patent number
US07718652B2

Reaction notes

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