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

HRID 1039191Notes

Reaction equation

HRID 1039191 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-2a381a48e74c4d5298ab156b8dd3a972
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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