Phosphorus oxybromide → 4-Bromo-6-methoxyquinoline

HRID 723540Notes

Reaction equation

HRID 723540 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2O.P(Br)(Br)([Br:16])=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:16][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178487890HCID 178487890, compound

Product 1

HCID 111607474-Bromo-6-methoxyquinolineYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

This was prepared by heating 6-methoxy-quinolin-4-ol (1 g) and phosphorus oxybromide (5 g) in chloroform (40 ml) under reflux for 18 hours. The mixture was cooled, basified with sodium bicarbonate, extracted with 5% methanol-chloroform, and dried (sodium sulfate). The product was chromatographed on silica gel (2-5% methanol-dichloromethane) to afford a solid (0.68 g).

Workup

  1. customThis was prepared
  2. temperatureunder reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with 5% methanol-chloroform
  5. dry with materialdried (sodium sulfate)
  6. customThe product was chromatographed on silica gel (2-5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-7aa06d75d8d248719510dd818c14ef47
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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