N-bromobutanimide → 3-Furancarboxylic acid, 5-methyl-2-phenyl-, ethyl ester

HRID 2398664Notes

Reaction equation

HRID 2398664 reaction equation
[C:1]([C:9](=[CH:15][CH2:16][CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:17][C:16]1[O:8][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 54331509HCID 54331509, compound

Product 1

HCID 100597273-Furancarboxylic acid, 5-methyl-2-phenyl-, ethyl esterYield 92.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4.65 g (0.02 mole) ethyl 2-benzoyl-2-pentenoate and 3.56 g (0.02 mole) N-bromosuccinimide in 50 ml of carbon tetrachloride was heated at reflux for 2 hours. After cooling, the succinimide was removed by filtration and the solution concentrated. Distillation of the crude product gave 4.25 g (92%) of ethyl 5-methyl-2-phenyl-3-furoate, bp 133°-135° C. (0.6 mm).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. concentrationthe solution concentrated
  6. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-093d3abfe8d444baade488486e324a31
Source dataset
uspto-grants-1977_05
Patent number
US04025537

Reaction notes

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