Methanol → 2-amino-4,6-dibromophenol

HRID 2420204Notes

Reaction equation

HRID 2420204 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([Br:11])[C:5]=1[OH:12])([O-])=O.CO.[OH-].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>O>[NH2:1][C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([Br:11])[C:5]=1[OH:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 101469NSC 523891

Product 1

HCID 3518632-amino-4,6-dibromophenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 89 g. of 2-nitro-4,6-dibromo-phenol, 270 ml. of methyl alcohol, 50ml. of 30% NaOH aqueous solution and 2,400 ml. of demineralized water was heated up to 50°-55° C., obtaining a yellow solution. To this solution, 178 g. of Na2S2O3 were added in small portions, by keeping the temperature at 50° C. The reaction mixture was then stirred for 30 minutes by keeping the temperature at 65° C. and finally for 30 minutes at room temperature. By cooling, 44.2 g. of 2-amino-4,6-dibromo-phenol were obtained, having a melting point equal to 89°-92° C.

Workup

  1. additionA mixture of 89 g
  2. customobtaining a yellow solution
  3. customat 50° C
  4. customat 65° C.
  5. waitfinally for 30 minutes at room temperature
  6. temperatureBy cooling

Sources & evidence

ORD record
ord-1e0cab4d9a3f4f7b911d226c1ae62e6b
Source dataset
uspto-grants-1978_08
Patent number
US04110116

Reaction notes

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