Hydrochloric Acid → 5-Ethoxy-2-fluoro-4-nitrobenzoic acid

HRID 2234446Notes

Reaction equation

HRID 2234446 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](F)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21]([OH:23])[CH3:22].Cl>CN(C=O)C.O>[CH2:21]([O:23][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10796Cesium carbonateHCID 2463752,5-Difluoro-4-nitrobenzoic acid

Product 1

HCID 686832655-Ethoxy-2-fluoro-4-nitrobenzoic acidYield 110%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,5-difluoro-4-nitrobenzoic acid (Fluorochem; 1 g, 4.92 mmol) was stirred and dissolved in DMF (10 mL) and caesium carbonate (4.8 g, 14.7 mmol) was added followed by ethanol (2.3 g, 49.9 mmol). The resulting white mixture was stirred at ambient temperature for 3 hours, diluted with water, acidified to pH1 with 2N HCl (aq), extracted with EtOAc (×3). Combined extracts were washed with water, dried (MgSO4), filtered and evaporated to yield the title compound as a yellow solid (1.24 g, 100%).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washCombined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-29c75310506b45aca691251040961b8f
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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