Water → [2-[2-(N,N-Dimethylamino)ethoxy]phenyl]-2,2,2-trifluoroethanone

HRID 1700907Notes

Reaction equation

HRID 1700907 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])=[O:4].Cl.[CH3:15][N:16]([CH2:18][CH2:19]Cl)[CH3:17].C1(C)C=CC=CC=1.O>CCOCC>[CH3:15][N:16]([CH2:18][CH2:19][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[C:2]([F:12])([F:13])[F:1])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 27611642-TrifluoroacetylphenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 18318999[2-[2-(N,N-Dimethylamino)ethoxy]phenyl]-2,2,2-trifluoroethanoneYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-trifluoroacetylphenol (380 mg, 2.0 mmol), 2-[N,N-dimethylamino]ethyl chloride, hydrochloride (432 mg, 6.0 mmol) potassium carbonate (1.38 g, 10 mmol) and toluene (5 ml) was refluxed for 3.5 h. After cooling to r.t., the mixture was treated with water and ether. The organic layer was washed twice with brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (acetone/ether 1:1 to 1:0) to give the title compound (375 mg, 72%) as a white solid.

Workup

  1. temperaturewas refluxed for 3.5 h
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (acetone/ether 1:1 to 1:0)

Sources & evidence

ORD record
ord-2576ed26ca4246f4af2d0e14fa96f104
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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