Sodium Carbonate → 4-Bromo-3-chloro-6-methoxyquinoline

HRID 638980Notes

Reaction equation

HRID 638980 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1O)=[CH:9][C:8]([O:13][CH3:14])=[CH:7][CH:6]=2.P(Br)(Br)[Br:16].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:16][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[N:4]=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 1784878763-Chloro-6-methoxyquinolin-4-ol

Product 1

HCID 224692724-Bromo-3-chloro-6-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-6-methoxy-quinolin-4-ol from above in dry DMF (80 mL) was cooled in ice and phosphorus tribromide (15.6 mL) added drop-wise, and the mixture was stirred, with ice-cooling for 30 minutes then allowed to warm to room temperature and stirred for a further 3.5 hours. It was cooled in ice and sodium carbonate solution was added and the solid was collected, washed well with water, and dried in vacuo, to afford a pale yellow solid (13.2 g). MS (ES) m/z 272/274/276 (M+H)+.

Workup

  1. temperaturecooling for 30 minutes
  2. stirringstirred for a further 3.5 hours
  3. temperatureIt was cooled in ice
  4. customthe solid was collected
  5. washwashed well with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a18e7d2c28044a6180f237c660882ad3
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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