Sodium Hydroxide → 4,7-Dibromofuro[3,2-c]pyridine

HRID 557173Notes

Reaction equation

HRID 557173 reaction equation
[Br:1][C:2]1[C:3]2[O:11][CH:10]=[CH:9][C:4]=2[C:5](=O)[NH:6][CH:7]=1.P(Br)(Br)([Br:14])=O.[OH-].[Na+]>ClC(Cl)C>[Br:14][C:5]1[C:4]2[CH:9]=[CH:10][O:11][C:3]=2[C:2]([Br:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 179855277-Bromofuro[3,2-c]pyridin-4(5H)-one

Product 1

HCID 179854894,7-Dibromofuro[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Combine 7-bromo-5H-furo[3,2-c]pyridin-4-one (16.16 g, 75.5 mmol), dichloroethane (160 mL), and phosphorus oxybromide (100 g, 348.8 mmol) and heat at reflux for about 2 hours. Cool to room temperature and pour the reaction mixture into ice water (1 L). Adjust the pH to 8 with 5N NaOH, extract into dichloromethane, wash with brine, dry over magnesium sulfate, filter, and concentrate. Purification by flash chromatography, eluting with hexane:ethyl acetate gives the title compound as a white solid.

Workup

  1. temperatureat reflux for about 2 hours
  2. extractionextract into dichloromethane
  3. washwash with brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurification by flash chromatography
  8. washeluting with hexane

Sources & evidence

ORD record
ord-4bb00674253e4e7c8cd93dcef1204bc2
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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