Phenol → 6-Bromo-1-phenoxyisoquinoline

HRID 2304230Notes

Reaction equation

HRID 2304230 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][CH:6]=[CH:5]2.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+].[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:7][CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 996PhenolHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 222502446-Bromo-1-chloro-isoquinoline

Product 1

HCID 226658626-Bromo-1-phenoxyisoquinolineYield 98.6%

Conditions

Temperature
140 °C

Procedure

A mixture of 10 g of 1b, 31 g of phenol and 4 g of KOH was heated at 140° C. for 2 hours. After cooling to room temperature aqueous 3N NaOH was added and the mixture was extracted with dichloromethane. The dichloromethane extract was washed with aqueous 2N NaOH, washed with water, dried (MgSO4) and concentrated to yield 12.2 g of 1c. 1H-NMR 200 MHz (CDCl3) δ: 7.1-7.6 (6H, m), 7.70 (1H, dd, J=9 Hz and J=2 Hz), 7.95-8.10 (2H, m), 8.31 (1H, d, J=9 Hz).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with aqueous 2N NaOH
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ebb823e8eed645baa920383b938dab85
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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