2,5-Hexanedione → HCID 23154931, compound

HRID 1912884Notes

Reaction equation

HRID 1912884 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]2[CH3:13])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 678524-Bromo-3-(trifluoromethyl)aniline

Product 1

HCID 23154931HCID 23154931, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

In 50 mL of toluene, 3.6 g (15 mmol) of 4-bromo-3-(trifluoromethyl)aniline was dissolved, and 2.06 g (18 mmol) of 2,5-hexanedione and 54 mg (0.28 mmol) of p-toluenesulfonic acid-hydrate were added thereto and the mixture solution was refluxed with stirring for two hours. The reaction solution was partitioned between a saturated sodium bicarbonate solution and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=9:1) to obtain 4.66 g (97%) of a target product as a pale yellow oil.

Workup

  1. temperaturethe mixture solution was refluxed
  2. customThe reaction solution was partitioned between a saturated sodium bicarbonate solution and ethyl acetate
  3. washthe organic layer was washed with a saturated sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-d1ebb4252d884c90b02b290f7959462c
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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