Nitric Acid → HCID 21220416, compound

HRID 1584813Notes

Reaction equation

HRID 1584813 reaction equation
[Br:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[C:3]=1[O:13][CH3:14].[N+:15]([O-])([OH:17])=[O:16].C(OCC)C.CCCCCC>S(=O)(=O)(O)O>[Br:1][C:2]1[C:10]([F:11])=[C:9]([N+:15]([O-:17])=[O:16])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[C:3]=1[O:13][CH3:14]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 8058HexaneHCID 21220435HCID 21220435, compound

Product 1

HCID 21220416HCID 21220416, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In 8 ml of sulfuric acid was dissolved 2.0 g of 4-bromo-2,5-difluoro-3-methoxybenzoic acid, and 4 ml of nitric acid was dropwise added to the solution with ice-cooling, after which the resulting mixture was stirred at room temperature for one hour. The reaction mixture was added to a mixed solvent of 50 ml of diethyl ether and 50 ml of ice water, and the organic layer formed was separated, washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. To the residue thus obtained was added n-hexane, and the resulting crystals were collected by filtration to obtain 1.9 g of pale yellow, crystalline 4-bromo-2,5-difluoro-3-methoxy-6-nitrobenzoic acid.

Workup

  1. additionwas dropwise added to the solution with ice-
  2. temperaturecooling
  3. customthe organic layer formed
  4. customwas separated
  5. washwashed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure
  8. customTo the residue thus obtained
  9. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-e56bdddda72d45e19ed5b62708faafe3
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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