Phenol → HCID 68567043, compound

HRID 2246582Notes

Reaction equation

HRID 2246582 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)[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[O:28]([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)[N:5]=[CH:4][N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 210750954-Chloro-6-(trifluoromethyl)quinazoline

Product 1

HCID 68567043HCID 68567043, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Example 5, Alternative Preparation, Step 1: A sample of 4-chloro-6-(trifluoromethyl)quinazoline (3.25 g, 13.97 mmol) was dissolved in acetonitrile (60 mL) under N2 atmosphere. The resultant cloudy solution was charged with Cs2CO3 (6.83 g, 20.96 mmol) and phenol (1.578 g, 16.77 mmol) and stirred at room temperature. After ˜65 hours, the reaction was filtered to remove the solids. The organic phase was concentrated in vacuo to yield an orange solid. The material was purified by automated flash chromatography (80 g silica gel) using 1:3 EtOAc/Hexanes as the eluant to afford the desired 4-phenoxy-6-(trifluoromethyl)quinazoline as a crystalline solid. LC/MS found (M+H)+=291.1.

Workup

  1. customExample 5, Alternative Preparation, Step 1
  2. filtrationthe reaction was filtered
  3. customto remove the solids
  4. concentrationThe organic phase was concentrated in vacuo
  5. customto yield an orange solid
  6. customThe material was purified by automated flash chromatography (80 g silica gel)

Sources & evidence

ORD record
ord-c9fbaf8771df4b94ac71a97e9bde9bf8
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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