Nitric Acid → 4-Fluoro-3-nitrobenzoic acid

HRID 1527456Notes

Reaction equation

HRID 1527456 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1>OS(O)(=O)=O>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 99734-Fluorobenzoic Acid

Product 1

HCID 679874-Fluoro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Conc. HNO3 (79 mL) was dropwise added to a solution of 4-fluoro-benzoic acid (70 g, 0.5 mol) in conc. H2SO4 (500 mL) at 0° C. The mixture was stirred for 4 h at RT and then poured into ice-water (3.0 L). The precipitate was filtered off, washed twice with water (0.5 L) and dried to give the title compound as a white solid. 1H-NMR (300 MHz, CDCl3): δ (ppm) 11.0 (s, br, 1H), 8.86 (m, 1H), 8.42 (m, 1H), 7.47 (m, 1H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed twice with water (0.5 L)
  3. customdried

Sources & evidence

ORD record
ord-71cb5804897b4c01b04461fbd163a703
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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