Potassium Hydroxide → 4-Cyano-2-fluorobenzoic acid

HRID 2041485Notes

Reaction equation

HRID 2041485 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[C:5]([F:13])[CH:4]=1)#[N:2].[OH-].[K+]>C(O)C.O>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:13])[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15278726Methyl 4-cyano-2-fluorobenzoate

Product 1

HCID 5906594-Cyano-2-fluorobenzoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dissolve methyl 4-cyano-2-fluoro-benzoate (2.9 g, 16.2 mmol) in absolute ethanol (100 mL). Add potassium hydroxide (4.5 g, 80.2 mmol) and stir the milky white mixture for 1.5 h. Dilute the mixture with water (125 mL) and wash with diethyl ether (50 mL). Collect the aqueous layer and concentrate in vacuo until solids start to appear in the flask, then adjust the mixture to pH 1 with concentrated HCl. Extract the aqueous mixture with diethyl ether (3×500 mL). Combine the organic extracts and concentrate in vacuo to obtain the desired intermediate as a white solid (2.2 g, 83%).

Workup

  1. washwash with diethyl ether (50 mL)
  2. customCollect the aqueous layer
  3. concentrationconcentrate in vacuo until solids
  4. extractionExtract the aqueous mixture with diethyl ether (3×500 mL)
  5. concentrationCombine the organic extracts and concentrate in vacuo

Sources & evidence

ORD record
ord-1e961e4870844ae29c6906cd7068b7fb
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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