Water → 4-(4-Azidomethylbenzyl)-nitrobenzene

HRID 2121027Notes

Reaction equation

HRID 2121027 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 (3×). The organic phase was washed with water (3×), 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 (3×)
  2. washThe organic phase was washed with water (3×)
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. washChromatography on silica gel, eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-2a27f440a9ba42e3983a0ddaa9777d22
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

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