Nitric Acid → 4-Fluoro-2-methyl-3-nitrobenzoic acid

HRID 1639801Notes

Reaction equation

HRID 1639801 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])=[C:8]([CH3:15])[CH:7]=1>>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[C:7]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 38606394-Fluoro-2-methylbenzoic acid

Product 1

HCID 534306954-Fluoro-2-methyl-3-nitrobenzoic acidYield 98%

Conditions

Temperature
7.5 °C

Procedure

To fuming nitric acid (20.3 mL, 409 mmol) was slowly added dropwise 4-fluoro-2-methylbenzoic acid (4.50 g, 29.2 mmol) while maintaining the temperature of the reaction mixture at 5-10° C. The reaction solution was stirred at 0-5° C. for 1 hr, and poured into ice. The precipitated solid was recovered, washed with water, and dried under reduced pressure to give 4-fluoro-2-methyl-3-nitrobenzoic acid (5.70 g, purity 25%) as a crudely purified product.

Workup

  1. additionpoured into ice
  2. customThe precipitated solid was recovered
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d9f17e8c8837422ba17ab20483744e16
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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