Dimethylformamide → 2-Bromonicotinaldehyde

HRID 361791Notes

Reaction equation

HRID 361791 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.CN(C)[CH:18]=[O:19].[Cl-].[NH4+]>C1COCC1>[Br:9][C:10]1[C:15]([CH:18]=[O:19])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamide

Product 1

HCID 47149512-Bromonicotinaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium diisopropylamide (1.0M in THF, 12.6 mmol) is added to a stirring solution of 2-bromopyridine (2.0 g, 12.6 mmol) in THF (10 ml) at -78° under nitrogen. The resulting mixture is stirred at -78° for two hours followed by addition of dimethylformamide (12.6 mmol) in THF (5 ml) at -78°. The mixture is allowed to warm to 20°-25°, poured into a saturated aqueous solution of ammonium chloride (100 ml), and extracted with ethyl acetate (3×50 ml). The organic phases are combined, dried over sodium sulfate and solvent removed under reduced pressure. The resulting residue is purified via flash chromatography (silica gel; hexane/ethyl acetate (4/1)) to give the title compound, mp 74°-76°; NMR (CDCl3) 7.45, 8.19, 8.59, 10.35δ; MS (EI, m/e) 185 (M+).

Workup

  1. temperatureto warm to 20°-25°
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialdried over sodium sulfate and solvent
  4. customremoved under reduced pressure
  5. customThe resulting residue is purified via flash chromatography (silica gel; hexane/ethyl acetate (4/1))

Sources & evidence

ORD record
ord-3dac298743ec414f89d48fcd2229aff2
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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