1,2-Dibromoethane → HCID 21833679, compound

HRID 2292666Notes

Reaction equation

HRID 2292666 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 962WaterSolvent2×

Procedure

To a mixture of 4-(1-pyrazolyl)methylphenol (15 g), 32.35 g of 1,2-dibromoethane and water (150 ml) was added dropwise an aqueous solution of sodium hydroxide (4.13 g) dissolved in water (30 ml) while stirring under heating at reflux over 30 minutes. The reaction mixture was then heated at reflux under stirring for further 1 hour, and then cooled to room temperature, which was extracted with diethyl ether (300 ml). The organic layer was washed with 5N aqueous sodium hydroxide solution and then water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 2-[4-(1-pyrazolyl)methylphenoxy]ethyl bromide (11.44 g) as white crystals. Yield, 47%.

Workup

  1. temperatureunder heating
  2. temperatureat reflux over 30 minutes
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux
  5. stirringunder stirring for further 1 hour
  6. extractionwhich was extracted with diethyl ether (300 ml)
  7. washThe organic layer was washed with 5N aqueous sodium hydroxide solution
  8. dry with materialwater, dried with anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-06caa3b9fcde44b1a0e5970ccf252d3b
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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