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

HRID 1785561Notes

Reaction equation

HRID 1785561 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-544195d3ef3c4d3499786c1c851a4cdb
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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