Methyl iodide → HCID 19703163, compound

HRID 861414Notes

Reaction equation

HRID 861414 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([CH3:14])[N:9]=2)=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH3:15])[N:10]([CH3:14])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178481729HCID 178481729, compound

Product 1

HCID 19703163HCID 19703163, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(4-bromophenyl)-5-hydroxy-1-methylpyrazole (2.5 g), acetone (200 ml), potassium carbonate (1.6 g) and methyl iodide (1.4 g) was heated at reflux for 2 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by flash column chromatography on silica gel using 10% ethyl acetate/toluene as eluent to give 3-(4-bromophenyl)-5-methoxy-1-methypyrazole (590 mg) as a solid, m.p. 71°-73° C.; NMR: 3.6(3H,s), 3.9(3H,s), 6.2(1H,s), 7.5-7.6(2H,d) and 7.6-7.7(2H,d).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by flash column chromatography on silica gel using 10% ethyl acetate/toluene as eluent

Sources & evidence

ORD record
ord-2d7bd01b1a2f4621bfb2fae3cfdf3afb
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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