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

HRID 1947895Notes

Reaction equation

HRID 1947895 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 81%

Conditions

Temperature
80 °C

Procedure

A solution of 2,5-difluoro-4-nitrobenzoic acid (1.88 g, 9.26 mmol) in MeOH (18.8 mL) was charged with potassium hydroxide (1.55 g, 27.7 mmol) in two batches. The reaction mixture was stirred at 80° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and then acidified with HCl. The resulting precipitate was filtered, washed with water and dried to give the product as a light yellow powder, 1.61 g (81% yield). This material was used in successive reaction without any further purification. 1H NMR (DMSO-d6, 400 MHz): δ=3.92 (s, 3H), 7.47 (d, J=5.56 Hz, 1H), 7.83 (d, J=9.09 Hz, 1H). MS (ES+): m/z 214.01 [MH−] (TOF, polar).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-80c047ebadb04191869c5c912c8ccb48
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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