Sodium Hydroxide → 2,4-Dibromo-3-(2-ethoxyiminopropyloxy)benzoic acid

HRID 585329Notes

Reaction equation

HRID 585329 reaction equation
[Br:1][C:2]1[C:12]([O:13][CH2:14][C:15](=[N:17][O:18][CH2:19][CH3:20])[CH3:16])=[C:11]([Br:21])[CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>C1COCC1.O>[Br:1][C:2]1[C:12]([O:13][CH2:14][C:15](=[N:17][O:18][CH2:19][CH3:20])[CH3:16])=[C:11]([Br:21])[CH:10]=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 85873781Ethyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoate

Product 1

HCID 858737862,4-Dibromo-3-(2-ethoxyiminopropyloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.820 g (1.90 mmol) of ethyl 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoate was dissolved in a mixture of 8 ml of THF and 8 ml of water, and 0.085 g (2.10 mmol) of NaOH was added. The mixture was stirred at RT for 12 h and then evaporated to dryness. The residue was taken up in water, and 6 N HCl was added. The mixture was then extracted with methylene chloride. The organic phase was dried using Na2SO4 and concentrated, giving 2,4-dibromo-3-(2-ethoxyiminopropyloxy)benzoic acid in the form of a colorless viscous oil.

Workup

  1. additionwas added
  2. customevaporated to dryness
  3. addition6 N HCl was added
  4. extractionThe mixture was then extracted with methylene chloride
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-547d34cf8ed64ba88e800683e9965501
Source dataset
uspto-grants-2005_08
Patent number
US06930208B2

Reaction notes

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