Sodium Azide → 2-Azido-1-[4-(benzyloxy)phenyl]ethan-1-one

HRID 2167840Notes

Reaction equation

HRID 2167840 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16]Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>C(Cl)Cl.O.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[N:19]([CH2:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)=[O:18])=[N+:20]=[N-:21]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 714163332-Azido-1-[4-(benzyloxy)phenyl]ethan-1-oneYield 94.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(4-benzyloxy-phenyl)-2-bromo-ethanone (28.55 g; 93.6 mmol) in CH2Cl2 (300 mL) and water (30 mL) was added nBu4NBr (1.51 g; 4.7 mmol) and NaN3 (6.69 g; 102.9 mmol) in one portion. After 4 h at RT, the layers were separated. The organic layer was washed water, dried (Na2SO4), filtered and concentrated in vacuo to afford 2-azido-1-(4-benzyloxy-phenyl)-ethanone (23.64 g).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60179543711944ff83cd6d04f49cb4e5
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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