Sodium Azide → 2-Azido-1-(2-methoxyphenyl)ethanone

HRID 1616577Notes

Reaction equation

HRID 1616577 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])=[O:8]>CS(C)=O.O>[N:1]([CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])=[O:8])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 123440Bromomethyl 2-methoxyphenyl ketone

Product 1

HCID 252236542-Azido-1-(2-methoxyphenyl)ethanoneYield 84.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Add sodium azide (2.14 g, 32.92 mmol) to a solution of 2-bromo-2′-methoxyacetophenone (5.01 g, 21.87 mmol) in 75 ml of DMSO. Stir the mixture at ambient temperature for 18 hours and dilute it with 250 ml of water. Extract the mixture with ether (3×). Dry the combined organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford 3.54 g of 2-azido-1-(2-methoxyphenyl)-ethanone.

Workup

  1. extractionExtract the mixture with ether (3×)
  2. dry with materialDry the combined organic layers with MgSO4
  3. filtrationFilter off the drying agent
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-2e47b4cd475d456b8c0b774f11c07a12
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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