1-(2-Methoxy-5-trifluoromethylphenyl)ethanone → HCID 82634870, compound

HRID 1257453Notes

Reaction equation

HRID 1257453 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13](=[O:15])[CH3:14].[Br-:16].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>C(OCC)C.C(=O)([O-])O.[Na+]>[Br:16][CH2:14][C:13]([C:4]1[CH:5]=[C:6]([C:9]([F:11])([F:10])[F:12])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:15]

Participants

5

Reactant 2

HCID 99426011-(2-Methoxy-5-trifluoromethylphenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 82634870HCID 82634870, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-[2-methoxy-5-(trifluoromethyl)phenyl]ethanone (1.00 g, 4.60 mmol) in diethyl ether (15 mL) was added phenyltrimethylammonium tribromide (1.78 g, 4.60 mmol), and the mixture was stirred overnight. The reaction mixture was diluted with diluted aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (1.35 g, 98%) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c17e50be416b4ddbaca8eeeaa6bfcb0f
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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