Sodium Azide → (3-Azidopropyl)(triphenyl)phosphanium bromide

HRID 2036270Notes

Reaction equation

HRID 2036270 reaction equation
[Br-].[Br:2][CH2:3][CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>C(O)C.O>[Br-:2].[N:25]([CH2:3][CH2:4][CH2:5][P+:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2723862(3-Bromopropyl)triphenylphosphonium bromide

Product 1

HCID 53362697(3-Azidopropyl)(triphenyl)phosphanium bromide

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

(3-Bromo-propyl)-triphenyl-phosphonium bromide was dissolved in ethanol/water (1/1). To it sodium azide was added. The reaction mixture was heated up to reflux overnight. Solvents were removed by evaporation. The residue was extracted by dry ethanol. Filtered and evaporated to give crude (3-azido-propyl)-triphenyl-phosphonium bromide and was used directly for the next step reaction without further purification.

Workup

  1. temperatureThe reaction mixture was heated up
  2. temperatureto reflux overnight
  3. customSolvents were removed by evaporation
  4. extractionThe residue was extracted by dry ethanol
  5. filtrationFiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ad8f3d5f84e949449b76dfa1c4991a85
Source dataset
uspto-grants-2013_11
Patent number
US08575176B2

Reaction notes

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