Hydrochloric Acid → HCID 16785176, compound

HRID 2101190Notes

Reaction equation

HRID 2101190 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].F[C:11]1[CH:12]=[CH:13][C:14]([N+:20]([O-:22])=[O:21])=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[N+:20]([C:14]1[CH:13]=[CH:12][C:11]([O:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17])([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 16785176HCID 16785176, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 2,4-difluorophenol 4 (20 g, 153.9 mmol), 5-fluoro-2nitrobenzoic acid 5, (28.5 g, 153.9 mmol), and cesium carbonate (100 g, 307.7 mmol) in DMF (310 mL) was heated in a 100° C. oil bath for 10 hrs. At the completion of the reaction, the mixture was cooled down to room temperature and was treated with 1 N HCl solution to bring pH to acidic, and was extracted with ethyl acetate. The organic layer was washed three times with 300 mL of water, dried, and concentrated to yield 32 g of 2-nitro-5-(2,4-difluorophenoxy)benzoic acid 6 as a brown solid.

Workup

  1. customAt the completion of the reaction
  2. temperaturethe mixture was cooled down to room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed three times with 300 mL of water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b26d6720dba34acaba1ded0c71f7c127
Source dataset
uspto-grants-2009_08
Patent number
US07572783B2

Reaction notes

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