1-Acetoxy-2-bromoethane → 2-Azidoethyl acetate
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
Product 1
Reagents, catalysts & solvents 2
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
- extractionextracted with ether
- washThe extracts were washed with water
- dry with materialbrine, dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-be79e0f3ff3b4a35963770befe98b1fd
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029391B2
Reaction notes
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