Dimethylamine → 4-(Dimethylamino)-2-(trifluoromethyl)benzaldehyde

HRID 1040389Notes

Reaction equation

HRID 1040389 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH3:14][NH:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:14][N:15]([CH3:16])[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehyde

Product 1

HCID 713728924-(Dimethylamino)-2-(trifluoromethyl)benzaldehydeYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 4-fluoro-2-trifluoromethylbenzaldehyde (500 mg, 2.60 mmol), dimethylamine (5.5 mol/L in ethanol, 0.95 mL, 5.2 mmol), potassium carbonate (360 mg, 2.6 mmol) in 5.2 mL of N,N-dimethylformamide was stirred at 110° C. overnight in a sealed tube. After the reaction mixture was diluted with water, the solution was extracted with ether. The extract was washed with 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=85/15 to 75/25) to obtain the title compound as a pale yellow powder (393 mg, 70%).

Workup

  1. extractionthe solution was extracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=85/15 to 75/25)

Sources & evidence

ORD record
ord-47696a39f748424c8358cbf8292945b0
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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