Potassium Carbonate → 4-Bromo-2-(dimethylamino)benzaldehyde

HRID 1854718Notes

Reaction equation

HRID 1854718 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][NH:18][CH3:19].C(O)C>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:18]([CH3:19])[CH3:17])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 22184060Dimethylamine ethanol

Product 1

HCID 433646554-Bromo-2-(dimethylamino)benzaldehydeYield 81.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 4-bromo-2-fluorobenzaldehyde (500 mg, 2.46 mmol) and potassium carbonate (340 mg, 2.46 mmol) in 5 mL of dry N,N-dimethylformamide was added dimethylamine/ethanol solution (0.67 mL, 5.6 M, 3.8 mmol) at room temperature. After being stirred at 110° C. overnight, the reaction mixture was diluted with ethyl acetate. The solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound as a yellow oil (458 mg, 81%).

Workup

  1. washThe solution was washed with water, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-acbbb45c6da04607a313cd03b2d195f1
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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