Hydrochloric Acid → Methyl 4-cyano-2-fluorobenzoate

HRID 2355276Notes

Reaction equation

HRID 2355276 reaction equation
Cl.O1CCOC[CH2:3]1.[C:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([F:19])[CH:11]=1)#[N:9]>CO>[CH3:3][O:15][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][C:10]([C:8]#[N:9])=[CH:11][C:12]=1[F:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 5906594-Cyano-2-fluorobenzoic acid

Product 1

HCID 15278726Methyl 4-cyano-2-fluorobenzoateYield 62.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 4N hydrochloride in 1,4-dioxane (100 mL, 400 mmol) to 4-cyano-2-fluoro-benzoic acid (10.0 g, 60.5 mmol) in methanol (100 mL). Stir the reaction mixture at room temperature overnight. Concentrate the reaction mixture. Purify the residue by column chromatography (silica gel) eluting with 20% ethyl acetate/hexane to give the title compound (6.8 g, 38.0 mmol).

Workup

  1. concentrationConcentrate the reaction mixture
  2. customPurify the residue by column chromatography (silica gel)
  3. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-47a78e55036f476db708790975ee9366
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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