1-Acetoxy-2-bromoethane → 2-Azidoethyl acetate

HRID 572532Notes

Reaction equation

HRID 572532 reaction equation
[C:1]([O:4][CH2:5][CH2:6]Br)(=[O:3])[CH3:2].[N-:8]=[N+:9]=[N-:10].[Na+]>CN(C)C=O.O>[C:1]([O:4][CH2:5][CH2:6][N:8]=[N+:9]=[N-:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 135641-Acetoxy-2-bromoethaneHCID 33557Sodium Azide

Product 1

HCID 120185192-Azidoethyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-bromoethyl acetate (500 μl, 4.54 mmol) in N,N-dimethylformamide (DMF) (2.0 mL) was treated with sodium azide (295 mg, 4.54 mmol) and then heated to 70° C. for 2 hours. The mixture was diluted with water and then extracted with ether. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated to afford the title compound as a colorless liquid. 1H NMR (400 MHz, CHLOROFORM-d) d=4.29-4.19 (m, 2 H), 3.53-3.44 (m, 2 H), 2.11 (s, 3 H).

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with water
  3. dry with materialbrine, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be79e0f3ff3b4a35963770befe98b1fd
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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