4-Bromophenol → HCID 22132637, compound

HRID 1857106Notes

Reaction equation

HRID 1857106 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:20]1[CH:21]=[CH:22][C:17]([Br:16])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 78084-BromophenolHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium Bicarbonate

Product 1

HCID 22132637HCID 22132637, compoundYield 501.2%

Conditions

Temperature
180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (1.00 g) and commercially available 4-bromophenol (115 mg) were mixed and stirred at 180° C. for 40 minutes. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate and then partitioned between water and chloroform, and the chloroform layer was washed with brine and dried with sodium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel, eluting in sequence with hexane/acetone, chloroform and chloroform/methanol, to obtain 1.20 g of the title compound (yield: 76%).

Workup

  1. custompartitioned between water and chloroform
  2. washthe chloroform layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. customAfter removing the solvent
  5. distillationby reduced-pressure distillation
  6. customthe resulting residue was purified by column chromatography on silica gel
  7. washeluting in sequence with hexane/acetone, chloroform and chloroform/methanol

Sources & evidence

ORD record
ord-c7e06160b751461aa4743e411a6cf356
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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