Water → HCID 58905134, compound

HRID 272588Notes

Reaction equation

HRID 272588 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([O:23][C:17]2[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=2[F:15])[CH:3]=[CH:4][C:5]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 171018Methyl 5-chloro-2-nitrobenzoate

Product 1

HCID 58905134HCID 58905134, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl 5-chloro-2-nitrobenzoate (73 g, 0.34 mol), 2,4-difluorophenol (51.1 g, 0.39 mol) and potassium carbonate (73 g, 0.53 mol) in NMP (200 mL) were stirred at 160° C. for 2 h. The reaction mixture was cooled to room temperature poured into water (250 mL) and extracted into EtOAc (2×100 mL). The organic layer was washed several times with water, dried over sodium sulfate, concentrated in vacuo, and the residue was purified by flash chromatography eluting with hexane: EtOAc (95:5) to yield 66.8 g of 5-(2,4-difluoro-phenoxy)-2-nitro-benzoic acid methyl ester (1A).

Workup

  1. extractionextracted into EtOAc (2×100 mL)
  2. washThe organic layer was washed several times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash chromatography
  6. washeluting with hexane: EtOAc (95:5)

Sources & evidence

ORD record
ord-ee1e0a634b96497085862afb3d34438a
Source dataset
uspto-grants-2008_11
Patent number
US07456185B2

Reaction notes

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