Water → HCID 58542585, compound

HRID 1843085Notes

Reaction equation

HRID 1843085 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:6]([CH3:13])[N:5]=1.[Br:15]Br.O.S(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:15][C:8]1[C:4]([O:3][CH:2]([F:1])[F:14])=[N:5][N:6]([CH3:13])[C:7]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 23665763Sodium BisulfiteHCID 58542532HCID 58542532, compound

Product 1

HCID 58542585HCID 58542585, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 700 mg (3.39 mmol) of methyl 3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate in 20 ml of chloroform is admixed dropwise with a solution of 570 mg (3.56 mmol) of bromine in 10 ml of chloroform and then stirred for three days at room temperature. The reaction mixture is added to 80 ml of water with some sodium bisulfite and shaken. The organic phase is separated off, dried over magnesium sulphate, filtered and concentrated by evaporation in vacuo: 792 mg of methyl 4-bromo-3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate (82%) are produced as white crystals.

Workup

  1. stirringshaken
  2. customThe organic phase is separated off
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-04e79c421fa142ceb339f41e896601ab
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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