Hydrochloric Acid → HCID 21708228, compound

HRID 651402Notes

Reaction equation

HRID 651402 reaction equation
[Cl:1][C:2]1[C:12]([Br:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].C1COCC1.[OH-].[Na+].Cl>C(O)C.O>[Cl:1][C:2]1[C:12]([Br:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15907523HCID 15907523, compound

Product 1

HCID 21708228HCID 21708228, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

26.63 g (86.3 mmol ) of ethyl 2-chloro-3-bromo-5-nitrobenzoate was dissolved in a mixture comprising 150 ml of ethanol and 80 ml. of THF, followed by the addition of 55 ml of a 2N aqueous solution of sodium hydroxide. The obtained mixture was stirred at room temperature for one hour, followed by the addition of water and 19 ml. of 6N hydrochloric acid. The obtained mixture was concentrated under reduced pressure and extracted with ethyl acetate. The ethyl acetate phase was washed with a saturated aqueous solution of common salt, dried and distilled to remove the solvent, giving 24.11 g of the title compound (yield: quantitative).

Workup

  1. concentrationThe obtained mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phase was washed with a saturated aqueous solution of common salt
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent

Sources & evidence

ORD record
ord-3c5876fcd28246c1a06818b815ab3b3e
Source dataset
uspto-grants-2001_08
Patent number
US06281214B1

Reaction notes

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