Water → 3-Chloro-2-fluoro-6-nitrophenol

HRID 851082Notes

Reaction equation

HRID 851082 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[OH-:13].[Na+].O>CS(C)=O>[Cl:9][C:6]1[C:7]([F:8])=[C:2]([OH:13])[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2230811,3-Dichloro-2-fluoro-4-nitrobenzene

Product 1

HCID 131885853-Chloro-2-fluoro-6-nitrophenolYield 35.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

10.5 g (0.05 mol) of 2,4-dichloro-3-fluoronitrobenzene was dissolved in 30 ml of dimethyl sulfoxide, and 8 ml of a 10% aqueous solution of sodium hydroxide was added to the mixture, followed by stirring the mixture at a temperature of 60° to 70° C. for 20 hours. After completion of the reaction, 200 ml of water was added thereto and the unreacted starting material was removed by extraction with diethyl ether. The aqueous layer was made acidic with acetic acid and extracted with diethyl ether. The ether extract was dried over sodium sulfate and the ether was distilled off. The resulting residue was purified by silica gel (100 g) column chromatography using chloroform as an eluant to provide 3,4 g (35.5% yield) of 3-chloro-2-fluoro-6-nitrophenol with m.p. 73° C.

Workup

  1. additionwas added
  2. customwas removed by extraction with diethyl ether
  3. extractionextracted with diethyl ether
  4. extractionThe ether extract
  5. dry with materialwas dried over sodium sulfate
  6. distillationthe ether was distilled off
  7. customThe resulting residue was purified by silica gel (100 g) column chromatography

Sources & evidence

ORD record
ord-d6f7a75693fa49ceab6e910bf9d79074
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Reaction notes

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