Sodium Azide → 4-Bromocinnamoyl azide

HRID 1067229Notes

Reaction equation

HRID 1067229 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12](Cl)=[O:13])=[CH:8][CH:7]=1>O.CC(C)=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[CH:11][C:12]([N:1]=[N+:2]=[N-:3])=[O:13])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 534112933-(4-Bromophenyl)prop-2-enoyl chloride

Product 1

HCID 539034244-Bromocinnamoyl azideYield 93.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium azide (NaN3) (2.2 g, 33.8 mmol) in water (7.5 mL) was added dropwise over 5 min to a stirred solution of 4-bromocinnamoyl chloride (22.2 mmol) in acetone (22 mL) at −10° C. The heterogeneous mixture was stirred at 0° C. for 1 h and diluted with water (25 mL). The precipitate was collected by filtration and dried in vacuo over phosphorus pentoxide (P2O5) to give 4-bromocinnamoyl azide (5.22 g, 20.7 mmol) as a golden-coloured solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. dry with materialdried in vacuo over phosphorus pentoxide (P2O5)

Sources & evidence

ORD record
ord-38f9ceefa761476880d6a26cfb145d81
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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