Hydrochloric Acid → 4-(2,3-Dibromopropoxy)pyridin-3-ol

HRID 1793309Notes

Reaction equation

HRID 1793309 reaction equation
[Br:1][CH:2]([CH2:15][Br:16])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[O:11]COC.Cl>C(O)C>[Br:1][CH:2]([CH2:15][Br:16])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[OH:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22020934HCID 22020934, compound

Product 1

HCID 220209444-(2,3-Dibromopropoxy)pyridin-3-olYield 55.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate (8) (0.0248 mol), HCl (35.42 ml)and ethanol (40 ml) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. The concentrate was cooled on an ice-water bath. The mixture was neutralized with a saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried, filtered and evaporated till dryness. The residue was purified by open column chromatography (eluent: CH2Cl2; CH2Cl2/MeOH (98/2, 96/4 and 90/10)). The pure fractions were collected and the solvent was evaporated, yielding 4.27 g of (±)-4-(2,3-dibromopropoxy)-3-pyridinol (intermediate 9).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. temperatureThe concentrate was cooled on an ice-water bath
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated till dryness
  7. customThe residue was purified by open column chromatography (eluent: CH2Cl2; CH2Cl2/MeOH (98/2, 96/4 and 90/10))
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8fb04d6901e243ce83f9b846bd236967
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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