Bromopinacolone → 1-Azido-3,3-dimethylbutan-2-one

HRID 600798Notes

Reaction equation

HRID 600798 reaction equation
Br[CH2:2][C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[N-:9]=[N+:10]=[N-:11].[Na+]>CC(C)=O.[Cl-].[Na+].O>[N:9]([CH2:2][C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 21642BromopinacoloneHCID 33557Sodium Azide

Product 1

HCID 126690681-Azido-3,3-dimethylbutan-2-oneYield 100.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-bromopinacolone (0.5 mL, 3.7 mmol) and NaN3 (0.48 g, 7.38 mmol) in 50 mL acetone was stirred overnight at room temperature. It was then poured into brine and extracted with dichloromethane. The extracts were washed with brine, were dried over Na2SO4, filtered, and were evaporated to afford the title compound as a yellow oil (524 mg, 100%). 1H NMR (DMSO-d6) δ 4.39 (s, 2H), 1.10 (s, 9H); MS (DCI+) m/z 142 (M+H)+.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with brine
  3. dry with materialwere dried over Na2SO4
  4. filtrationfiltered
  5. customwere evaporated

Sources & evidence

ORD record
ord-39c19d511ad7451d8398c85b1d892944
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Reaction notes

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