Water → 4-(4-Azidomethylbenzyl)-nitrobenzene

HRID 1358813Notes

Reaction equation

HRID 1358813 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][C:7]1[CH:22]=[CH:21][C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1.O>CN(C)C=O>[N:1]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:21][CH:22]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 218770124-(4-Bromomethylbenzyl)-nitrobenzene

Product 1

HCID 218770044-(4-Azidomethylbenzyl)-nitrobenzeneYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (210 mg, 1.15 eq) was added to a solution of 4-(4-bromomethylbenzyl)-nitrobenzene (901 mg) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at room temperature for 2 hours, poured into water, and extracted with diethyl ether (3X). The organic phase was washed with water (3X), dried (MgSO4), and evaporated to dryness. Chromatography on silica gel, eluting with hexane/ethyl acetate, gave 4-(4-azidomethylbenzyl)-nitrobenzene (492 mg, 62%) as a yellow oil.

Workup

  1. extractionextracted with diethyl ether (3X)
  2. washThe organic phase was washed with water (3X)
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. washChromatography on silica gel, eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-02d9067674ca42abbb55e64d36a196cc
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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