Dimethylformamide → 5-Cyano-2-fluorobenzaldehyde

HRID 1058657Notes

Reaction equation

HRID 1058657 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.CN(C)[CH:24]=[O:25]>O1CCCC1>[F:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[CH:24]=[O:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 145174-FluorobenzonitrileHCID 178418339Butyllithium

Product 1

HCID 109097255-Cyano-2-fluorobenzaldehydeYield 44.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylamine (0.35 mL, 2.5 mmol) was dissolved in tetrahydrofuran (3.5 mL) and the temperature was adjusted to 0° C. Then, n-butyllithium (hexane solution) (1.24 mL, 2.0 mmol) was dropped thereto, followed by stirring for 10 minutes. Thereafter the reaction temperature was brought to −78° C. 4-Fluorobenzonitile (0.2 g, 1.65 mmol) was added thereto, stirring for 1 hour. Then, dimethylformamide (0.19 mL, 2.5 mmol) was dropped thereto, followed by stirring for 20 minutes and then the conventional treatment was performed. The residue was purified by thin-layer chromatography (hexane: ethyl acetate=8:1), to give 2-fluoro-5-cyanobenzaldehyde (0.11 g, 43.4%).

Workup

  1. customwas adjusted to 0° C
  2. customwas brought to −78° C
  3. stirringstirring for 1 hour
  4. stirringby stirring for 20 minutes
  5. customThe residue was purified by thin-layer chromatography (hexane: ethyl acetate=8:1)

Sources & evidence

ORD record
ord-03c26ffb69d846d4a55bbbef8dac6276
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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