1,2-Dibromoethane → HCID 21833679, compound

HRID 1740826Notes

Reaction equation

HRID 1740826 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:14][CH2:15][CH2:16]Br.[OH-].[Na+]>O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:16][CH2:15][Br:14])=[CH:9][CH:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 1334121-(4-Hydroxybenzyl)pyrazole

Product 1

HCID 21833679HCID 21833679, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 15 g of 4-(1-pyrazolyl)methylphenol, 32.4 g of 1,2-dibromoethane and 150 ml of water was added dropwise 30 ml of an aqueous solution of 4.1 g of sodium hydroxide while stirring under heating at reflux over 2 hours. Then, after heating at reflux under stirring for further 30 minutes, the reaction mixture was poured into 200 ml of ice water, which was extracted twice with 100 ml of diethyl ether. The organic layers were combined, washed with 5N aqueous sodium hydroxide solution, water and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 11.44 g of 2-[4-(l-pyrazolyl)methylphenoxy]ethyl bromide as white crystals. Yield, 47%.

Workup

  1. temperatureunder heating
  2. temperatureat reflux over 2 hours
  3. temperatureThen, after heating
  4. temperatureat reflux
  5. stirringunder stirring for further 30 minutes
  6. extractionwas extracted twice with 100 ml of diethyl ether
  7. washwashed with 5N aqueous sodium hydroxide solution, water
  8. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7915e4f4fef449f08c29c693ae3d5f3e
Source dataset
uspto-grants-1999_10
Patent number
US05972949

Reaction notes

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