Ethyl Acetate → (2E)-3-(4-Bromo-2-furanyl)-2-propenoyl azide

HRID 920939Notes

Reaction equation

HRID 920939 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9](Cl)=[O:10])[O:5][CH:6]=1.[N-:12]=[N+:13]=[N-:14].[Na+].C(OCC)(=O)C>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]([N:12]=[N+:13]=[N-:14])=[O:10])[O:5][CH:6]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86683152HCID 86683152, compound

Product 1

HCID 86683153(2E)-3-(4-Bromo-2-furanyl)-2-propenoyl azideYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (E)-3-(4-bromofuran-2-yl)acryloyl chloride (4.0 g, 16.99 mmol) in 10 mL of 1,4-dioxane was added to a solution of sodium azide (2.21 g, 34.0 mmol) in 10 mL of water and 10 mL of 1,4-dioxane. The reaction mixture was stirred for 2.5 h at room temperature. The reaction mixture was mixed with ethyl acetate and water. Phases were separated and the aqueous phase was extracted with ethyl acetate (twice). The combined organic phases were washed with brine, dried, filtrated and concentrated to give 4 g of the title compound (yield: 97%).

Workup

  1. customPhases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-464f6a266ca64114a5917d6c99ab1b04
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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