Hydrogen Bromide → HCID 22992688, compound

HRID 1168550Notes

Reaction equation

HRID 1168550 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[N:7]([CH2:10][CH2:11][OH:12])=[N+:8]=[N-:9].Br.O>C(Cl)Cl.C(N(CC)CC)C>[Br:1][CH:2]([CH3:6])[C:3]([O:12][CH2:11][CH2:10][N:7]=[N+:8]=[N-:9])=[O:4]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 79047Propanoyl bromide, 2-bromo-HCID 1231182-Azidoethanol

Product 1

HCID 22992688HCID 22992688, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

The synthesis was carried out in methylene chloride at 0° C. A solution of 2-bromopropionyl bromide in methylene chloride was added dropwise to a mixture of 2-azidoethanol in methylene chloride, triethylamine was added to neutralize the formed hydrobromic acid. After stirring at room temperature over-night water was added and the organic layer was extracted three times with water, the organic phase was then dried and the solvent evaporated. The product was a mixture of byproducts and had to be separated via silica gel column producing pure 2-azidoethyl 2-bromopropionate. Characterization was made with 1H-NMR and FT-IR.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe organic layer was extracted three times with water
  4. customthe organic phase was then dried
  5. customthe solvent evaporated
  6. additiona mixture of byproducts
  7. customto be separated via silica gel column

Sources & evidence

ORD record
ord-9465d88d0cd34d148127a92d40f00200
Source dataset
uspto-grants-2003_09
Patent number
US06624262B2

Reaction notes

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