Phenol → 4-Phenoxy-6-chloropyrimidine

HRID 1005909Notes

Reaction equation

HRID 1005909 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=1.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[O:7]([C:15]1[CH:16]=[C:11]([Cl:10])[N:12]=[CH:13][N:14]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 115936774-Phenoxy-6-chloropyrimidineYield 57.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of phenol (1.1 g) in dimethylformamide (20 mL) was slowly added sodium hydride (60%, 805 mg) at 0° C. After the resultant mixture was stirred at 0° C. for 30 minutes, 4,6-dichloropyrimidine (1.5 g) was added, followed by stirring at 25° C. for 1 hour and then addition of saturated aqueous ammonium chloride solution (20 mL). Then, the obtained mixture was diluted with ethyl acetate (50 mL) and washed three times with brine (30 mL each time). An organic layer was separated, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The title compound (1.2 g) was obtained by silica gel column chromatography (ethyl acetate/n-hexane=1/10).

Workup

  1. customat 0° C
  2. washwashed three times with brine (30 mL each time)
  3. customAn organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e347c85cfc047b6bafe0cfde036ed7b
Source dataset
uspto-grants-2004_09
Patent number
US06787551B2

Reaction notes

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