4-Fluorobenzonitrile → Benzonitrile, p-imidazol-1-yl-

HRID 2042012Notes

Reaction equation

HRID 2042012 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[C:11]1[Na]>CN(C=O)C>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 145174-FluorobenzonitrileHCID 178507081HCID 178507081, compound

Product 1

HCID 135744Benzonitrile, p-imidazol-1-yl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture 4-fluorobenzonitrile (3 g, 25 mmol) and imidazolyl sodium (2.48 g, 27.5 mmol) in DMF (50 mL) was stirred at 80° C. under Ar for 12 h. Progress of reaction was monitored by TLC. The reaction mixture was concentrated in vacuo and the residue was diluted with 50 mL water and stirred. The aqueous mixture was extracted with EtOAc (2×50 mL). Combined EtOAc extracts was dried over anhydrous MgSO4, concentrated, and the 4-(1-imidazolyl)-benzonitrile was isolated by column chromatography (3.6 g, 78%). LCMS: MH+=170; 1H NMR (CDCl3) δ 8.0 (s, 1H), 7.5 (d, 2H), 7.4 (m, 3H), 7.3 (d, 1H)

Workup

  1. customProgress of reaction
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was diluted with 50 mL water
  4. extractionThe aqueous mixture was extracted with EtOAc (2×50 mL)
  5. dry with materialCombined EtOAc extracts was dried over anhydrous MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a231bdcd5f234bea807ff0788beba2b2
Source dataset
uspto-grants-2013_11
Patent number
US08586576B2

Reaction notes

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