6-Methoxyquinoline → 5-Bromo-6-methoxyquinoline

HRID 428537

Reaction equation

HRID 428537 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]=[CH:6]2.[Br:13]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Br:13][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2

Participants

5

Reactant 3

HCID 148606-MethoxyquinolineHCID 24408BromineHCID 23665763Sodium Bisulfite

Product 1

HCID 184141285-Bromo-6-methoxyquinolineYield 58.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-methoxyquinoline (5 g, 31.4 mmol) in acetic acid (50 mL) was slowly added Br2 neat (1.62 mL, 31.4 mmol). The reaction mixture was stirred at ambient temperature for 1 hour and then poured onto ice. Saturated aqueous sodium bisulfite was added, and the resulting slurry was extracted into EtOAc (2×200 mL). The organic fractions were combined, dried over Na2SO4, concentrated, and purified by column chromatography (5% MeOH/CH2Cl2) affording 4.39 g of the title compound as the acetate salt. The free base was prepared by washing the salt with 1 N NaOH (50 mL) and H2O (100 mL) and extracting into CH2Cl2 (200 mL). The organic fractions were concentrated affording 3.89 g (52%) of the title compound as a pink solid.

Workup

  1. additionpoured onto ice
  2. extractionthe resulting slurry was extracted into EtOAc (2×200 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-04db3afc05d0439e8c9082b013422ddd
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Linked notes

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