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

HRID 914084Notes

Reaction equation

HRID 914084 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].[OH-:16].[K+].[CH3:18]O>>[F:14][C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([O:16][CH3:18])=[CH:9][C:4]=1[C:3]([OH:2])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 18526058Methyl 2,5-difluoro-4-nitrobenzoate

Product 1

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

Conditions

Temperature
80 °C

Procedure

To a solution of methyl-2,5-difluoro-4-nitrobenzoate (10 g, 46 mmol) in methanol (100 mL) was added potassium hydroxide (7.73 g, 184 mmol) in two batches. The reaction mixture was stirred in an oil bath at 80° C. for 1 h. It was then concentrated, acidified with HCl. Solid was filtered, washed with water and dried to give the product as light yellow powder (10 g, quantitative yield). 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. concentrationIt was then concentrated
  2. filtrationSolid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-9aa9ad2880544829926e313f77ce0ae8
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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