Sodium Chloride → 2-Azido-1-(4-tert-butylphenyl)ethanone

HRID 1785532Notes

Reaction equation

HRID 1785532 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+].[Na+].[Cl-]>CC(C)=O>[N:15]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1)=[O:4])=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 33557Sodium AzideHCID 23247702-Bromo-1-(4-tert-butylphenyl)ethan-1-one

Product 1

HCID 866096112-Azido-1-(4-tert-butylphenyl)ethanoneYield 85.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the product of Example 1A (985 mg, 3.86 mmol) in 45 mL acetone was added NaN3 (0.505 g, 7.07 mmol), and the mixture stirred overnight at room temperature. The reaction mixture was poured into saturated NaCl solution and extracted with dichloromethane. The extracts were washed with saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo to afford the title compound as a yellow oil (715 mg, 85%). 1H NMR (DMSO-d6) δ 7.88 (d, 2H, J=8.5 Hz), 7.57 (d, 2H, J=8.5 Hz), 4.86 (s, 2H), 1.31 (s, 9H); MS (ESI+) m/z 218 (M+H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe extracts were washed with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d6baec4e8404978a184d19e768cdbb6
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

Loading…