Methanol → 2-Fluoro-5-methoxy-4-nitrobenzoic acid

HRID 1041479Notes

Reaction equation

HRID 1041479 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8](F)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][OH:16]>>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:16][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 887MethanolHCID 2463752,5-Difluoro-4-nitrobenzoic acid

Product 1

HCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acid

Conditions

Temperature
45 °C

Procedure

Into a round bottom flask, 2,5-difluoro-4-nitro-benzoic acid (5.00 g, 0.0246 mol) and methanol (20.0 mL, 0.494 mol;) was added. The reaction was heated at 45° C. for one hour. The solvent was removed under vacuum. 1N HCl was added to pH 4. The solid was filtered and washed with water to give 2-fluoro-5-methoxy-4-nitro-benzoic acid as an off white solid (2.84 g, 54%). 1H-NMR (DMSO-D6, 400 MHz): δ 13.90 (bs, 1H), 8.08 (d, 1H), 7.72 (d, 1H), 3.94 (s, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. addition1N HCl was added to pH 4
  3. filtrationThe solid was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-a694dab604854821b7e0420c4dbcd6af
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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