Bromine → HCID 22491738, compound

HRID 2180310Notes

Reaction equation

HRID 2180310 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([NH2:6])=[CH:4][C:3]=1[C:10]1[C:14]([Cl:15])=[C:13]([C:16]([F:19])([F:18])[F:17])[N:12]([CH3:20])[N:11]=1.C([O-])(=O)C.[Na+].[Br:26]Br>C(O)(=O)C>[Br:26][C:4]1[C:3]([C:10]2[C:14]([Cl:15])=[C:13]([C:16]([F:17])([F:18])[F:19])[N:12]([CH3:20])[N:11]=2)=[C:2]([F:1])[CH:8]=[C:7]([Cl:9])[C:5]=1[NH2:6]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 22491729HCID 22491729, compound

Product 1

HCID 22491738HCID 22491738, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

28 g (0.086 mol) of 4-fluoro-6-chloro-3-(4-chloro-5-trifluoromethyl-1-methyl-1H-pyrazol-3-yl)aniline (described in EP-A 0791571) were dissolved in 200 ml of acetic acid and admixed with 35 g (0.42 mol) of sodium acetate. 13.7 g (0.086 mol) of bromine were added dropwise to this mixture. The mixture was stirred overnight, the volatile components were removed under reduced pressure and the residue was taken up in 200 ml of dichloromethane. This solution was washed with 2 N aqueous NaOH and dried over MgSO4, and the residue obtained after concentration of the solution was chromatographed on silica gel using cyclohexane/ethyl acetate (4/1 v/v). This gave 20 g of the title compound IVc.1.

Workup

  1. customthe volatile components were removed under reduced pressure
  2. washThis solution was washed with 2 N aqueous NaOH
  3. dry with materialdried over MgSO4
  4. customthe residue obtained after concentration of the solution
  5. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-5e960d311f134f0e8a9e8f6f4f30d6e2
Source dataset
uspto-grants-2005_05
Patent number
US06888003B2

Reaction notes

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