Phenol → 6-Bromo-1-phenoxyisoquinoline

HRID 636910Notes

Reaction equation

HRID 636910 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
40 °C

Procedure

A mixture of 10 g of 1b, 31 g of phenol and 4 g of KOH was heated at 1 40° 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. customAfter -cooling to room temperature
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. extractionThe dichloromethane extract
  5. washwas washed with aqueous 2N NaOH
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-599230146c634a3ba44b1bc52c9d1291
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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