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

HRID 1748326Notes

Reaction equation

HRID 1748326 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-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-bromo-3,3-dimethylbutan-2-one (50 g, 279 mmol) in acetone (400 mL) is added NaN3 (22 g, 335 mmol) at 0° C. The reaction mixture is warmed to room temperature for 7 h. The reaction mixture is filtered and the filtrate is concentrated. The residue is diluted with EtOAc and washed with water and brine. The organic layer is dried (Na2SO4) and concentrated to afford the title crude compound which is used in the next step without purification.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. additionThe residue is diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41f168c034d346ccbc920474806e11c2
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…