Bromine → 2-Bromo-4,6-dichloro-3-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)aniline

HRID 2180313Notes

Reaction equation

HRID 2180313 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([C:10]2[CH:14]=[C:13]([O:15][CH:16]([F:18])[F:17])[N:12]([CH3:19])[N:11]=2)=[CH:5][C:3]=1[NH2:4].C([O-])(=O)C.[Na+].[Br:25]Br>C(O)(=O)C>[Br:25][C:5]1[C:6]([C:10]2[CH:14]=[C:13]([O:15][CH:16]([F:18])[F:17])[N:12]([CH3:19])[N:11]=2)=[C:7]([Cl:9])[CH:8]=[C:2]([Cl:1])[C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 224917312,4-Dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)aniline

Product 1

HCID 224917422-Bromo-4,6-dichloro-3-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)aniline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1 g (2.9 mmol) of 2,4-dichloro-5-(5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)aniline and 2.4 g (29 mmol) of sodium acetate were initially charged in 100 ml of glacial acetic acid, and 0.93 g (5.6 mmol) of bromine was added dropwise at room temperature. The reaction mixture was stirred overnight and then concentrated, and the residue was taken up in toluene and washed with 50 ml of 5% by weight strength aqueous sodium hydroxide solution until neutral. The organic phase was dried over magnesium sulfate and concentrated. This gave 1.3 g of the aniline IVa.4. The product that was obtained was identical to the compound obtained according to example 1.1.

Workup

  1. concentrationconcentrated
  2. washwashed with 50 ml of 5% by weight strength aqueous sodium hydroxide solution until neutral
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product that was obtained
  6. customobtained

Sources & evidence

ORD record
ord-5e5db62ea6674938b8bfef6a90013de4
Source dataset
uspto-grants-2005_05
Patent number
US06888003B2

Reaction notes

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