Toluene → HCID 86626774, compound

HRID 604015Notes

Reaction equation

HRID 604015 reaction equation
C1(C)C=CC=CC=1.F[C:9]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=1[CH:11]=[O:12].Cl.[CH3:22][NH:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH3:22][N:23]([CH3:24])[C:9]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:10]=1[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 86626774HCID 86626774, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To toluene (5 ml) are added 2-fluoro-5-trifluoromethyl-benzaldehyde (650 mg) and dimethylamine hydrochloride (2.76 g), followed by addition of potassium carbonate (1.4 g), and the mixture is stirred at 120° C. overnight. The reaction solution is cooled to room temperature, and thereto are added ethyl acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=49:1→4:1) to give 2-dimethylamino-5-trifluoromethyl-benzaldehyde (529 mg). MS (m/z): 218 [M+H]+

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=49:1→4:1)

Sources & evidence

ORD record
ord-337a66a75157461a8f8c6025511b43ea
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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