Nitric Acid → 5-Fluoro-2-nitrobenzoic acid

HRID 439319Notes

Reaction equation

HRID 439319 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10]>S(=O)(=O)(O)O>[F:5][C:6]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[C:8]([CH:7]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 99683-Fluorobenzoic Acid

Product 1

HCID 27374205-Fluoro-2-nitrobenzoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Fuming nitric acid (6.0 mL) was added to concentrated sulfuric acid (60 mL) at 0° C. and stirred for several minutes. To this solution was added 3-fluorobenzoic acid (5.60 g, 40 mmol) over 30 minutes and the reaction was allowed to continue for another 6 hours in an ice bath. The reaction was poured onto cracked ice, and the precipitate was collected by filtration and dried to give 5-fluoro-2-nitrobenzoic acid (7.20 g, 97%) as a white solid.: m.p. 118°-120°; 1H NMR (400 MHz, DMSO-d6) δ 7.62 (dt, 1H), 7.71 (dd, 1H), 8.14 (dd, 1H); 13C NMR (100 MHz, DMSO-d6) δ 117.1, 117.4, 119.2, 119.5, 127.6, 127.7, 131.5, 131.6, 144.5, 162.9, 165.4, 165.6.

Workup

  1. additionThe reaction was poured
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-66eff921e4fe486e8a51fedcb2e52dd3
Source dataset
uspto-grants-1996_05
Patent number
US05514676

Reaction notes

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