Benzyl Bromide → Benzyl azide

HRID 1709687Notes

Reaction equation

HRID 1709687 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:9]=[N+:10]=[N-:11].[Na+]>C(O)C>[CH2:1]([N:9]=[N+:10]=[N-:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 33557Sodium Azide

Product 1

HCID 12152Benzyl azideYield 144.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction of this crude benzyl bromide (6.7 g) and sodium azide (1.92 g) in ethanol (90 ml) at reflux as in Example 33 yielded 5.7 g of crude benzyl azide. Chromatography on silica gel afforded 3.98 g of pure 4-(trichlorovinyl)benzyl azide.

Workup

  1. temperatureat reflux as in Example 33

Sources & evidence

ORD record
ord-de27a4678e474ef79a08175be7b6ff1b
Source dataset
uspto-grants-1990_08
Patent number
US04950673

Reaction notes

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