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

HRID 1855209Notes

Reaction equation

HRID 1855209 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>[N:9]([CH2:2][C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])=[N+:10]=[N-:11]

Participants

4

Reactant 2

HCID 21642BromopinacoloneHCID 33557Sodium Azide

Product 1

HCID 126690681-Azido-3,3-dimethylbutan-2-oneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 2 L three-necked round-bottom flask fitted with a mechanical stirrer was added bromopinacolone A-1 (134 g, 747 mmol, 1.0 equiv), acetone (1.2 L), and sodium azide (63.2 g, 971 mmol, 1.3 equiv). The reaction mixture was stirred at room-temperature overnight and then filtered, and the solids were washed with acetone (2×100 mL). The filtrate was concentrated in vacuo to provide azidopinacolone (105.0 g, 100%) as an oil. The crude material was used in the next step without further purification.

Workup

  1. customTo a 2 L three-necked round-bottom flask fitted with a mechanical stirrer
  2. filtrationfiltered
  3. washthe solids were washed with acetone (2×100 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-686d792cef614ebe8e38e935c49d1432
Source dataset
uspto-grants-2015_02
Patent number
US08962855B2

Reaction notes

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