Acetic Acid → 5-Bromo-2,3-dimethylbenzoic acid

HRID 337614Notes

Reaction equation

HRID 337614 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[N+]([O-])(O)=O.[Br:20]Br>O.[N+]([O-])([O-])=O.[Ag+]>[Br:20][C:12]1[CH:13]=[C:14]([CH3:15])[C:6]([CH3:5])=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 117822,3-Dimethylbenzoic acidHCID 24408Bromine

Product 1

HCID 668959895-Bromo-2,3-dimethylbenzoic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

To a stirred acetic acid solution (0.2 M) of 2,3-dimethylbenzoic acid (1 eq.) was added sequentially nitric acid (12 eq.), water (25 eq.) and bromine (1.1 eq.). Finally, silver nitrate (1 M aqueous solution, 1.3 eq.) was added dropwise over a period of 30 min. After another hour of stirring at RT, the crude reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were then washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Trituration of the crude product thus obtained in hexanes afforded the title compound as a yellow solid.

Workup

  1. customthe crude reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were then washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customTrituration of the crude product thus obtained in hexanes

Sources & evidence

ORD record
ord-37e33c4d6ec0494685f67ce10f914856
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…