Water → Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate

HRID 1169353Notes

Reaction equation

HRID 1169353 reaction equation
[O-]CC.[Na+].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16].O>C(O)C.C1(C)C=CC=CC=1>[N:14](/[C:17](=[CH:10]\[C:9]1[CH:12]=[CH:13][C:6]([Br:5])=[CH:7][CH:8]=1)/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16]

Participants

7

Reactant 4

HCID 962WaterHCID 69480Acetic acid, azido-, ethyl esterHCID 707414-BromobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 24767341Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoateYield 39%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent2×

Procedure

Into a solution of sodium ethoxide (a 20% solution in ethanol, 22.2 g) in toluene (100 ml) was added at 0° C. over a period of more than 10 minutes a solution of 4-bromobenzaldehyde (10 g) and ethyl azidoacetate (7.0 g) in toluene (50 ml). After being stirred at room temperature for 2 hours, the reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate/hexane 1:19) to obtain ethyl (Z)-2-azido-3-(4-bromophenyl)acrylate (6.24 g) as a yellow oily substance.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialwas dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was subjected to separation and purification

Sources & evidence

ORD record
ord-b5f4680863cc4c45a60cd640bde76739
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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