Methyl Ethyl Ketone → methyl 4-((5-bromo-1H-pyrazol-1-yl)methyl)benzoate

HRID 1399807Notes

Reaction equation

HRID 1399807 reaction equation
[Br:1][C:2]1[NH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.CC(=O)CC>C(OCC)(=O)C>[Br:1][C:2]1[N:6]([CH2:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 256687Methyl 4-(bromomethyl)benzoateHCID 12014433-bromo-1H-pyrazole

Product 1

HCID 21106857methyl 4-((5-bromo-1H-pyrazol-1-yl)methyl)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-bromo-1H-pyrazole (146 mg, 1 mmol), methyl 4-(bromomethyl)benzoate (242 mg, 2 mmol) and K2C03 (276 mg, 2 mmol) were placed in a 100-mL flask with 2-butanone (20 mL) and heated at reflux temperature for 17 h. The mixture was cooled, filtered and evaporated in vacuuo leaving a residue which was dissolved in ethyl acetate and washed with water. The separated organic layer was dried and concentrated to give desired product as an oil (188 mg, 100% yield). This crude material was used without further purification. LCMS (m/z): 295.1 [M+H]+

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 17 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customevaporated in vacuuo
  6. customleaving a residue which
  7. washwashed with water
  8. customThe separated organic layer was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-73cf6090848e404e8b502687850da8c0
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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