Hydrogen Bromide → HCID 9891091, compound

HRID 429327Notes

Reaction equation

HRID 429327 reaction equation
Cl.N[C:3]1[CH:4]=[C:5]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:26]([F:29])([F:28])[F:27])=[N:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N([O-])=O.[Na+].[BrH:34]>O.[Cu]Br>[Br:34][C:3]1[CH:4]=[C:5]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:26]([F:29])([F:28])[F:27])=[N:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 18355386HCID 18355386, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 9891091HCID 9891091, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 962WaterSolvent

Procedure

To a solution of 1-(3-amino-4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)pyrazole hydrochloride (0.80 g) in ca. 24% hydrobromic acid (16 ml) was added a solution of sodium nitrite (0.14 g) in water (1 ml) while the internal temperature of the reaction mixture was maintained below 0° C. The above mixture was added to an ice-cooled solution of copper(I) bromide (0.30 g) in ca. 24% hydrobromic acid (8 ml) and the mixture was stirred at ambient temperature for 1.5 hours. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with chloroform) to give the product, which was recrystallized from diisopropyl ether (3 ml)-ethyl acetate (3 ml) to give 1-(3-bromo-4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-pyrazole (0.39 g).

Workup

  1. temperaturewas maintained below 0° C
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (elution with chloroform)
  7. customto give the product, which
  8. customwas recrystallized from diisopropyl ether (3 ml)-ethyl acetate (3 ml)

Sources & evidence

ORD record
ord-5aea6e7703dc48efb9d40fe3667e45b9
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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