Phenacyl bromide → 2-Azido-1-phenylethanone

HRID 2357059Notes

Reaction equation

HRID 2357059 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.CCOC(C)=O>[N:11]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 33557Sodium Azide

Product 1

HCID 109865532-Azido-1-phenylethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To the desired bromo-acetophenone (from last step, 1.0 equivalents), in DMF (10 mL) was added NaN3 (0.24 g, 3.0 equiv). The resulting mixture was then stirred in DMF for 1 hour. The reaction mixture was diluted with EtOAc (50 mL) and washed with H2O (2×50). The solvent removed in vacuo and the product was purified by silica gel column chromatography using the Combi-Flash system (Hex:EtOAc) to give the azido-acetophenone product as a white solid in 99% (0.44 g) yield. TLC (4:1, Hex/EtOAc), Rf=0.4.

Workup

  1. washwashed with H2O (2×50)
  2. customThe solvent removed in vacuo
  3. customthe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-84b5ce1925cd462684857b50bcf7af7d
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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