Allyl bromide → HCID 23331860, compound

HRID 903900Notes

Reaction equation

HRID 903900 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH:7]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH:8]([OH:13])[C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25].[Na]>O1CCOCC1>[CH2:25]([O:13][CH:8]([C:9]([CH3:11])([CH3:12])[CH3:10])[CH:7]([O:6][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:20][CH:19]=1)[N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)[CH:24]=[CH2:23]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 5360545SodiumHCID 12766906HCID 12766906, compound

Product 1

HCID 23331860HCID 23331860, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

34 g (0.1 mol) of 1-(4-bromophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol were suspended in 175 ml of dioxane and the suspension was added dropwise to a mixture of 3.5 g of 80% strength sodium hydride and 125 ml of dioxane while stirring. Thereafter, the mixture was heated under reflux for one hour. After cooling, 14.5 g (0.12 mol) of allyl bromide were added dropwise at room temperature to the sodium salt thus obtained. The mixture was then heated under reflux for 15 hours, allowed to cool and concentrated by distilling off the solvent. The oily residue was taken up in 600 ml of methylene chloride and the methylene chloride solution was washed twice with 1,000 ml of water each time, dried over sodium sulphate and concentrated. The residue was distilled under a high vacuum. 30 g (79% of theory) of 2-allyloxy-1-(4-bromophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butane of boiling point 152°-154° C./0.2 mm Hg were obtained.

Workup

  1. temperatureThereafter, the mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureAfter cooling
  4. customthus obtained
  5. temperatureThe mixture was then heated
  6. temperatureunder reflux for 15 hours
  7. temperatureto cool
  8. concentrationconcentrated
  9. distillationby distilling off the solvent
  10. washthe methylene chloride solution was washed twice with 1,000 ml of water each time
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated
  13. distillationThe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-95d89c183bf44e2aba283834225d2e9f
Source dataset
uspto-grants-1980_10
Patent number
US04229459

Reaction notes

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