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

HRID 914220Notes

Reaction equation

HRID 914220 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, 3H) 7.66 (d, J=4 Hz, 1H) 8.01 (d, J=8 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-ee8705c0e308412f8ab6906b15f73e06
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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