2-Chloro-1-fluoro-4-nitrobenzene → HCID 68885745, compound

HRID 399470Notes

Reaction equation

HRID 399470 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[SH:17]>>[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S:17][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 178527877HCID 178527877, compound

Product 1

HCID 68885745HCID 68885745, compoundYield 13%

Procedure

Using an analogous procedure to that described in the first paragraph of the portion of Example 8 which is concerned with the preparation of starting materials, 3-chloro-4-fluoronitrobenzene was reacted with 2-imidazolethiol to give a precipitated solid which was partitioned between methylene chloride and 2 h aqueous sodium hydroxide solution. The aqueous phase was acidified by the addition of a concentrated (20%) aqueous citric acid solution and the precipitate was isolated and dried. The material was recrystallised from a mixture of hexane and ethyl acetate to give 2-chloro-4-nitrophenyl 2-imidazolyl sulphide in 13% yield.

Workup

  1. customto give a precipitated solid which
  2. customwas partitioned between methylene chloride and 2 h aqueous sodium hydroxide solution
  3. additionThe aqueous phase was acidified by the addition of
  4. concentrationa concentrated (20%) aqueous citric acid solution
  5. customthe precipitate was isolated
  6. customdried
  7. customThe material was recrystallised from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-1bb14dde9fbf4a2b9dfc535c767fae60
Source dataset
uspto-grants-1998_10
Patent number
US05821246

Reaction notes

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