Sodium Azide → 1-(Azidomethyl)-4-methoxybenzene
Reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>C(#N)C>[N:11]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-(chloromethyl)-4-methoxybenzene (20 g, 128 mmol) and sodium azide (12.5 g, 192 mmol) in acetonitrile (255 mL) was refluxed for 5 h under N2 atmosphere. The mixture was filtered and concentrated in vacuo. The residue was diluted with DCM, washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo to afford crude 1-(azidomethyl)-4-methoxybenzene. The residue was used for the next reaction without further purification.
Workup
- temperaturewas refluxed for 5 h under N2 atmosphere
- filtrationThe mixture was filtered
- concentrationconcentrated in vacuo
- additionThe residue was diluted with DCM
- washwashed with H2O and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fc28325b20f2478a9afe2ef9177b7065
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741906B2
Reaction notes
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