Bromine → HCID 178440430, compound

HRID 1076447Notes

Reaction equation

HRID 1076447 reaction equation
C([O-])(=O)C.[Na+].[CH:6]([C:9]1[CH:13]=[CH:12][NH:11][N:10]=1)([CH3:8])[CH3:7].[Br:14]Br>C(O)(=O)C.O>[Br:14][C:13]1[C:9]([CH:6]([CH3:8])[CH3:7])=[N:10][NH:11][CH:12]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 178439403HCID 178439403, compound

Product 1

HCID 178440430HCID 178440430, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of sodium acetate (19.7 g., 0.24 mole) in acetic acid (100 ml.) and water (15 ml.), 3-isopropylpyrazole (11.0 g., 0.1 mole) was added, followed by dropwise addition of bromine (16.0 g., 0.11 mole) keeping the internal temperature below 15° C. The mixture was kept at 25° C. for 15 hours, treated with water (200 ml.) and extracted with ethyl ether (3 × 50 ml.), and the ether layer washed with water (1 × 50 ml.) dried, (sodium sulfate) and evaporated under reduced pressure. The resultant pale yellow oil was distilled to give 4-bromo-3-isopropylpyrazole (15.3 g., 81%) with a boiling point of 85° C. at 0.06 mm Hg.

Workup

  1. customthe internal temperature below 15° C
  2. extractionextracted with ethyl ether (3 × 50 ml.)
  3. washthe ether layer washed with water (1 × 50 ml.)
  4. customdried
  5. custom(sodium sulfate) and evaporated under reduced pressure
  6. distillationThe resultant pale yellow oil was distilled

Sources & evidence

ORD record
ord-9eb2d99f85eb462da8cecf91b53ad0f4
Source dataset
uspto-grants-1976_05
Patent number
US03957480

Reaction notes

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