Sodium Hydroxide → HCID 12881150, compound

HRID 1902586Notes

Reaction equation

HRID 1902586 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Br:26])[C:23]([Cl:27])=[CH:22][C:21]=1[OH:28].[OH-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:7]=1[O:28][C:21]1[CH:22]=[C:23]([Cl:27])[C:24]([Br:26])=[CH:25][C:20]=1[Cl:19]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 160224-Bromo-2,5-dichlorophenolHCID 13102542HCID 13102542, compound

Product 1

HCID 12881150HCID 12881150, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 28.4 gm of 4,5-dichloro-2-nitro-1-phenoxy-benzene, 24.2 gm of 2,5-dichloro-4-bromo-phenol, 10 ml of 10 N sodium hydroxide and 80 ml of dimethylsulfoxide was stirred for 5 hours at 100° C. Thereafter, the reaction mixture was stirred into 700 ml of 1 N sodium hydroxide, the mixture was allowed to stand overnight at room temperature, the liquid phase was decanted, and the precipitated product was taken up in chloroform. The chloroform solution was washed with water, dried with sodium sulfate and evaporated, and the residue was recrystallized from a mixture of 200 ml ethanol and 2 ml dimethylformamide. 36.5 gm (75% of theory) of the light yellow crystalline title compound, m.p. 85° C., were obtained.

Workup

  1. waitto stand overnight at room temperature
  2. customthe liquid phase was decanted
  3. washThe chloroform solution was washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. customthe residue was recrystallized from a mixture of 200 ml ethanol and 2 ml dimethylformamide

Sources & evidence

ORD record
ord-55237b03e38b4bd9a6c4a47b4978979c
Source dataset
uspto-grants-1982_12
Patent number
US04364875

Reaction notes

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