Allyl bromide → HCID 54426531, compound

HRID 260305Notes

Reaction equation

HRID 260305 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([OH:11])=[O:10])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH:7]=[CH:8][C:9]([O:11][CH2:23][CH:22]=[CH2:21])=[O:10])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 683902-Propenoic acid, 3-(3-nitrophenyl)-

Product 1

HCID 54426531HCID 54426531, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Nitrocinnamic acid (5.0, 25.9 mM) was dissolved in DMF (50 ml), and anhydrous K2CO3 (7.15 g, 51.8 mM) added with stirring. Allyl bromide (3.36 ml, 38.8 mM) was run in, and the mixture stirred for 18 hours at ambient temperature. After filtration, the solvent was evaporated, the residue treated with water, and product extracted into diethyl ether (2 ×100 ml). The organic solution was washed with an aqueous solution of NaHCO3, water, and brine, and dried (MgSO4). Evaporation of the solvent gave title compound (6 g).

Workup

  1. stirringstirred for 18 hours at ambient temperature
  2. filtrationAfter filtration
  3. customthe solvent was evaporated
  4. additionthe residue treated with water, and product
  5. extractionextracted into diethyl ether (2 ×100 ml)
  6. washThe organic solution was washed with an aqueous solution of NaHCO3, water, and brine
  7. dry with materialdried (MgSO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-74b1d690609340388400d9ae61cd96b7
Source dataset
uspto-grants-1996_06
Patent number
US05527791

Reaction notes

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