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

HRID 914255Notes

Reaction equation

HRID 914255 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].[OH-:15].[K+].[CH3:17]O>>[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:15][CH3:17])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2463752,5-Difluoro-4-nitrobenzoic acid

Product 1

HCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acidYield 90%

Procedure

To a solution of 2,5-difluoro-4-nitrobenzoic acid (55 g, 291 mmol) in methanol (800 mL) at 80° C. was added a methanolic solution of potassium hydroxide (48.9 g, 873 mmol in 175 mL MeOH, pre-heated at 80° C. to dissolve) dropwise in a period of 2 h using an addition funnel. The reaction mixture was continuously stirred for 1 h after addition was completed. It was then concentrated, acidified with HCl to pH=1-2. The reaction mixture was then vigorously stirred overnight. Fine powder was filtered, washed with more water and dried to give the product as light yellow powder (55.4 g, 90%). 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). [M+H] calc'd for C8H6FNO5, 216. found 216.

Workup

  1. additionafter addition
  2. concentrationIt was then concentrated
  3. customvigorously stirred overnight
  4. filtrationFine powder was filtered
  5. washwashed with more water
  6. customdried

Sources & evidence

ORD record
ord-753e46229e6b4038b6b2a077f830b6b5
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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