Sodium Hydroxide → 5-Cyano-4-fluoro-2-methoxy-benzoic acid

HRID 457982Notes

Reaction equation

HRID 457982 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[C:7]([F:12])=[CH:6][C:5]=1[O:13][CH3:14].[OH-].[Na+]>C(O)C>[C:10]([C:8]1[C:7]([F:12])=[CH:6][C:5]([O:13][CH3:14])=[C:4]([CH:9]=1)[C:3]([OH:15])=[O:2])#[N:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53419729Methyl 5-cyano-4-fluoro-2-methoxybenzoate

Product 1

HCID 184682175-Cyano-4-fluoro-2-methoxy-benzoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirring suspension of 5-cyano-4-fluoro-2-methoxy-benzoic acid methyl ester (2.98 g, 14.25 mmol) in ethanol (30 mL, 0.5 M) was treated with 1.25 M NaOH (68 mL, 85.5 mmol). Within 10 minutes, the solution was clear and by TLC, all of the starting material was consumed. The solution was concentrated and then treated with 2N HCl until the pH was 1. The white precipitate formed was collected by suction filtration, dissolved in dioxane, and was washed with aq saturated NaCl. The organic layer was dried over Na2SO4, filtered and concentrated to afford 5-cyano-4-fluoro-2-methoxy-benzoic acid (1.9 g, 70%) as a white solid. Rf=0.34 (20% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 8.13 (d, J=8.1 Hz, 1 H), 7.36 (d, J=12.0 Hz, 1 H), 3.90 (s, 3 H).

Workup

  1. customall of the starting material was consumed
  2. concentrationThe solution was concentrated
  3. additiontreated with 2N HCl until the pH was 1
  4. customThe white precipitate formed
  5. filtrationwas collected by suction filtration
  6. dissolutiondissolved in dioxane
  7. washwas washed with aq saturated NaCl
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c1536a2892f6446084a4df7bd760e96b
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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