Benzyl Bromide → Benzyl azide

HRID 882876Notes

Reaction equation

HRID 882876 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5](Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CS(C)=O>[CH2:5]([N:1]=[N+:2]=[N-:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 33557Sodium Azide

Product 1

HCID 12152Benzyl azideYield 88.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of sodium azide (7.6 g, 116.9 mmol), benzyl bromide (10 g, 58.4 mmol) in DMSO (80 mL) was stirred at room temperature for 18 h. The reaction mixture was then slowly poured into ice water and extracted with ether (3×200 mL). The combined organic extracts were washed with water and brine, dried (Na2SO4) and evaporated, giving the title compound as a colourless oil (6.9 g, 88% yield).

Workup

  1. extractionextracted with ether (3×200 mL)
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-47243aae181e4a4683a31a9a8317fb2b
Source dataset
uspto-grants-2012_08
Patent number
US08236809B2

Reaction notes

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