Sodium Methoxide → 2-Fluoro-5-methoxy-4-nitrobenzoic acid

HRID 1880991Notes

Reaction equation

HRID 1880991 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8](F)[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[F:14].[CH3:16][O-:17].[Na+]>CO>[F:14][C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([O:17][CH3:16])=[CH:9][C:4]=1[C:3]([OH:2])=[O:15]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18526058Methyl 2,5-difluoro-4-nitrobenzoate

Product 1

HCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acidYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl-2,5-difluoro-4-nitrobenzoate (1 g, 4.6 mmol) in methanol (10 mL) was added sodium methoxide (95%, 393 mg, 6.9 mmol). The reaction mixture was stirred at room temperature overnight. It was then concentrated, acidified with HCl. Solid was filtered and dried to give the product as light yellow powder (728 mg, 70%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.95 (s, 3 H) 7.66 (d, J=4 Hz, 1 H) 8.01 (d, J=8 Hz, 1 H).

Workup

  1. concentrationIt was then concentrated
  2. filtrationSolid was filtered
  3. customdried

Sources & evidence

ORD record
ord-2c9c261eec274a6ead678666b772773d
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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