Sodium Carbonate → methyl 3-[(4-bromo-1H-pyrazol-1-yl)methyl]benzoate

HRID 1468175Notes

Reaction equation

HRID 1468175 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Br:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.Br[CH2:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]>CC(N(C)C)=O>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][CH:24]=[C:15]([CH2:14][N:10]2[CH:9]=[C:8]([Br:7])[CH:12]=[N:11]2)[CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 163754-BromopyrazoleHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 17024610methyl 3-[(4-bromo-1H-pyrazol-1-yl)methyl]benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

Add sodium carbonate (5.80 g, 41.7 mmol) to a solution of 4-bromopyrazole (3.10 g, 20.9 mmol) and methyl 3-bromomethylbenzoate (4.8 g, 20.9 mmol) in 40 mL of dimethylacetamide. Stir the mixture at 60° C. overnight. Cool the reaction to room temperature and pour into 300 mL of ice water. Collect the resulting solid by filtration and dry to afford 6.0 g, 98% yield of 3-(4-bromo-pyrazol-1-ylmethyl)-benzoic acid methyl ester.

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. customCollect the resulting solid
  4. filtrationby filtration
  5. customdry

Sources & evidence

ORD record
ord-4e641c3e276744b3bbe37361bc3c6167
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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