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

HRID 1896884Notes

Reaction equation

HRID 1896884 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 (×3). 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 (×3)
  2. washThe organic fraction was washed with water, saturated NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-6c8ddd4d79be494b831179c52962f754
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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