3-Chlorophenol → HCID 22003583, compound

HRID 324513Notes

Reaction equation

HRID 324513 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[Br:11][C:12]1[N:13]([CH3:24])[C:14]([CH2:22]Br)=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1>CN(C)C=O>[Br:11][C:12]1[N:13]([CH3:24])[C:14]([CH2:22][O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 22003602HCID 22003602, compound

Product 1

HCID 22003583HCID 22003583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chlorophenol (1.73 g) in dry N,N-dimethylformamide (60 ml) was added 60% sodium hydride (0.535 g) in small portions. After the addition was complete the resultant solution was stirred at room temperature for 1 h. The product of step (i) (4.0 g) was added and the mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic phase was washed with saturated potassium carbonate solution (×2), saturated brine (×2) and dried (MgSO4). The solvent was removed under reduced pressure.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 16 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between water and dichloromethane
  5. washThe organic phase was washed with saturated potassium carbonate solution (×2), saturated brine (×2)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b0df58b1c4c54d1382ad3c2547574b0d
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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