Potassium Carbonate → 4-Bromo-7-methoxyquinoline

HRID 899972Notes

Reaction equation

HRID 899972 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:16])=O.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O>[Br:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24613Phosphorus oxybromideHCID 178487715HCID 178487715, compound

Product 1

HCID 215682924-Bromo-7-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

22.74 g of 4-hydroxy-7-methoxyquinoline are added to 200 g of phosphorus oxybromide preheated to a temperature in the region of 110° C. The reaction medium is heated at this same temperature for 3 hours. The reaction medium is poured, while hot, into a mixture of 500 ml of EtOAc and 500 ml of ice-cold water. The medium is neutralized with potassium carbonate to pH 7. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, evaporated under reduced pressure and then purified by column chromatography (SiO2, EtOAc/cyclohexane 50/50 by volume as eluents, Ar), and 14.6 g of the expected product are obtained.

Workup

  1. custompreheated to a temperature in the region of 110° C
  2. temperatureThe reaction medium is heated at this same temperature for 3 hours
  3. additionThe reaction medium is poured
  4. customAfter separation of the phases
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. custompurified by column chromatography (SiO2, EtOAc/cyclohexane 50/50 by volume as eluents, Ar), and 14.6 g of the expected product
  8. customare obtained

Sources & evidence

ORD record
ord-98769976f2a643e993380a823da3d69b
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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