Nitric Acid → HCID 22448999, compound

HRID 2186724Notes

Reaction equation

HRID 2186724 reaction equation
FC(F)(F)[C:3]([O:5][C:6](=O)[C:7](F)(F)F)=O.[N+:14]([O-:17])(O)=[O:15].[Br:18][C:19]1C=C(O)[C:22]([O:25]C)=[CH:23][CH:24]=1>C(OCC)(=O)C.[Cl-].[Na+].O>[Br:18][C:19]1[CH:7]=[C:6]([O:5][CH3:3])[C:22]([OH:25])=[C:23]([N+:14]([O-:17])=[O:15])[CH:24]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 9845Trifluoroacetic anhydrideHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 22448999HCID 22448999, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic anhydride (3.50 ml) was cooled to −78° C. 61% nitric acid (1.85 ml) was slowly added dropwise at −78° C., and the resultant mixture was stirred at 0° C. for 2.5 hours. The above nitrating agent was added to a solution of 4-bromoguaiacol (5.00 g) in ethyl acetate (50 ml) and the mixture was stirred at 0° C. for 1.5 hours. Saturated brine was added to the reaction solution, and an organic layer was then separated. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, concentrated, and then allowed to cool to form crystals. After filtration, the crystal was washed with a small amount of n-hexane, and then dried under reduced pressure to obtain the object compound (4.02 g, yield 66%).

Workup

  1. customan organic layer was then separated
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. temperatureto cool
  6. customto form crystals
  7. filtrationAfter filtration
  8. washthe crystal was washed with a small amount of n-hexane
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-a914201d33f04f70856d07a0c00b6fe2
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

Loading…