5-Amino-2-chlorophenol → 5-Amino-4-bromo-2-chlorophenol

HRID 539631Notes

Reaction equation

HRID 539631 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.[Br-:10].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.CO>[NH2:1][C:2]1[C:3]([Br:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1

Participants

5

Reactant 2

HCID 806765-Amino-2-chlorophenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 593778815-Amino-4-bromo-2-chlorophenolYield 18%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-chloro-phenol (15.85 g, 110.4 mmol) in dichloromethane (300 ml) and MeOH (150 ml) was added tetrabutylammonium tribromide (58.6 g, 121.4 mmol). The mixture was stirred at room temperature for 20 minutes, and then was partitioned between saturated aqueous Na2SO3 and Et2O. The organic layer was separated, washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash chromatography (hex:EtOAc/7:3) gave 5-amino-4-bromo-2-chloro-phenol (4.38 g, 18%) as a white solid.

Workup

  1. customwas partitioned between saturated aqueous Na2SO3 and Et2O
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the residue by flash chromatography (hex:EtOAc/7:3)

Sources & evidence

ORD record
ord-f1aaee6927154b5590ec709f572cbb6d
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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