Nitric Acid → Methyl 5-bromo-2-methyl-3-nitrobenzoic acid

HRID 2208748

Reaction equation

HRID 2208748 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[N+:18]([O-])([OH:20])=[O:19]>>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([N+:18]([O-:20])=[O:19])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 5557655-Bromo-2,4-dimethylbenzoic acid

Product 1

HCID 86623945Methyl 5-bromo-2-methyl-3-nitrobenzoic acidYield 91%

Conditions

Temperature
-10 °C

Procedure

5-Bromo-2,4-dimethylbenzoic acid (12 g, 52.17 mmol) was added to cooled conc. H2SO4 (48 mL) at −10° C. lot wise. After 10 minutes nitrating mixture {prepared as mixing Conc. HNO3 (6 mL) with conc.H2SO4 (24 mL)} was added drop wise at −10° C. Resulting reaction mass was stirred at −10° C. for 30 minutes. On completion, reaction mixture was poured on ice cold water, solid precipitated was filtered, washed with water and dried under vacuum giving desired compound (13 g, 91%).

Workup

  1. custommixture {prepared
  2. customResulting
  3. customreaction mass
  4. customOn completion, reaction mixture
  5. additionwas poured on ice cold water, solid
  6. customprecipitated
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-605d50c7682244c88c1ca871eeafdb64
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Linked notes

Loading…