Formaldehyde → 4-bromo-3-t-butyl-1H-pyrazole-1-ylmethanol

HRID 1983011Notes

Reaction equation

HRID 1983011 reaction equation
[Br:1][C:2]1[C:3]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:4][NH:5][CH:6]=1.[CH2:11]=[O:12]>C(N(CC)CC)C.CC(C)=O>[Br:1][C:2]1[C:3]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:4][N:5]([CH2:11][OH:12])[CH:6]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 178441971HCID 178441971, compound

Product 1

HCID 231491454-bromo-3-t-butyl-1H-pyrazole-1-ylmethanolYield 105.2%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 180AcetoneSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of 3.14 g of 4-bromo-3-t-butyl-1H-pyrazole, 0.93 g of paraformaldehyde and 0.11 g of triethylamine was stirred at 130° C. for 7 hours. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filtered. Hexane was added to the residue obtained by concentration of the filtrate under reduced pressure, as a result, a crystal was formed. The crystal was collected to obtain 3.79 g of 4-bromo-3-t-butyl-1H-pyrazole-1-ylmethanol.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. additionHexane was added to the residue
  4. customobtained by concentration of the filtrate under reduced pressure, as a result
  5. customa crystal was formed
  6. customThe crystal was collected

Sources & evidence

ORD record
ord-db0ca102a1c24264b3da0eab9fcbad8a
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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