N-methyl-2-pyrrolidone → 2,3-Difluoro-1-(2,6-difluoro-phenoxy)-4-nitro-benzene

HRID 13334

Reaction equation

HRID 13334 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].CN1CCCC1=O.[F:17][C:18]1[C:23]([F:24])=[C:22](F)[CH:21]=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[F:24][C:23]1[C:18]([F:17])=[C:19]([N+:26]([O-:28])=[O:27])[CH:20]=[CH:21][C:22]=1[O:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8]

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 943922,6-Difluorophenol

Product 1

HCID 231452862,3-Difluoro-1-(2,6-difluoro-phenoxy)-4-nitro-benzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

470 mg of 2,6-difluoro-phenol and 1.5 g of tetrabutylammonium bromide were added to an N-methylpyrrolidinone (13 ml) solution of 500 mg of 2,3,4-trifluoro-nitrobenzene, and the reaction liquid was stirred overnight at 130° C. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1) to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=4/1)
  7. customto obtain the entitled compound

Sources & evidence

ORD record
ord-11f1adab8b8e4535907931e7f083cac5
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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