Phenol → 2-Nitro-5-phenoxybenzoic acid

HRID 2099964Notes

Reaction equation

HRID 2099964 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:11]([C:5]1[CH:4]=[CH:3][C:2]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 142334252-Nitro-5-phenoxybenzoic acidYield 123.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 5-fluor-2-nitrobenzoic acid (2.6 g, 14.1 mmol, Aldrich Chemical Co., Milwaukee, Wis.) and phenol (1.5 g, 15.5 mmol, Aldrich Chemical Co., Milwaukee, Wis.) in DMF (70 mL) was treated with K2CO3 (5.9 g, 42.4 mmol) and heated to 120° C. for 6 hours. The reaction was cooled to room temperature and the solvent removed under reduced pressure. The resulting residue was dissolved in water and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaCl, dried (Na2SO4), filtered, and concentrated to afford 34A (4.5 g).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with saturated aqueous NaCl
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2b14770dff034d198dc6482d393ed224
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

Loading…