Phenol → 1-Phenoxy-7-(trifluoromethyl)isoquinoline

HRID 2175566Notes

Reaction equation

HRID 2175566 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[K+].[C:18]1([OH:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC>[O:24]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 585626771-Chloro-7-(trifluoromethyl)isoquinoline

Product 1

HCID 585624711-Phenoxy-7-(trifluoromethyl)isoquinoline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-chloro-7-(trifluoromethyl)isoquinoline (1.5 g, 6.5 mmol), from above step C, KOH (0.73 g, 13 mmol) and phenol (6.1 g, 65 mmol) were heated at 100° C. for 72 h. The resulting mixture was cooled to room temperature and taken in Et2O and extracted with 4N NaOH (x3). The organic fraction was washed with water, saturated NaCl, dried over Na2SO4 and evaporated to give the title compound.

Workup

  1. extractionextracted with 4N NaOH (x3)
  2. washThe organic fraction was washed with water, saturated NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-c2a5e4b325de4dbda9c8a0b76d1dfe8a
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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