Sodium Azide → 2-Azidomethylphenylacetic acid t-butyl ester

HRID 397476Notes

Reaction equation

HRID 397476 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14]Br)([CH3:4])([CH3:3])[CH3:2].[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][N:17]=[N+:18]=[N-:19])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 590858792-Bromomethylphenylacetic acid t-butyl ester

Product 1

HCID 590858722-Azidomethylphenylacetic acid t-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of crude 2-bromomethylphenylacetic acid t-butyl ester (0.349 mol) in 600 mL DMF was added 34.1 g (0.524 mol) sodium azide and the mixture stirred at 65° C. for 3 h. After cooling to ambient temperature, the mixture was diluted with 1.2 L ethyl acetate. The organic layer was washed with water (3×800 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give the titled compound as a yellow oil. This material was used without further purification.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. washThe organic layer was washed with water (3×800 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c9d03952f114f368b2b10883e5e2aac
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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