Sodium Hydroxide → 3-Fluoro-5-(methoxycarbonyl)benzoic acid

HRID 732004Notes

Reaction equation

HRID 732004 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4047226Dimethyl 5-fluoroisophthalate

Product 1

HCID 247289203-Fluoro-5-(methoxycarbonyl)benzoic acidYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 5-fluoro-isophthalic acid dimethyl ester (1.7 g, 8.0 mmol) in methanol (41 ml) was treated with 1.0 N sodium hydroxide (7.2 ml, 7.2 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1.0 N HCl to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulphate. After removal of solvent in vacuo, a total of 1.3 g (83%) of 5-fluoro-isophthalic acid monomethyl ester was isolated as a white solid. 1H NMR (DMSO), δ (ppm): 8.31 (t, 1H), 7.96 (m, 2H), 3.91 (s, 3H).

Workup

  1. waitThe reaction was left
  2. concentrationAfter the solution was concentrated
  3. dissolutionthe residue was dissolved in water
  4. customtransferred to a separatory funnel
  5. washThe aqueous layer was washed with dichloromethane (3 times)
  6. extractionto extract the precipitate, which
  7. washwas then washed with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. customAfter removal of solvent in vacuo

Sources & evidence

ORD record
ord-19b3f5fd1e7c48a484c8e349f1fe1a1a
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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