Hydrogen Bromide → HCID 86618356, compound

HRID 1441702Notes

Reaction equation

HRID 1441702 reaction equation
BrN1C(=[O:7])CCC1=O.[BrH:9].[C:10]([CH:18]([CH2:24][C:25](Br)=[CH2:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O.C(OCC)C>[C:10]([C:18](=[CH:24][C:25](=[O:7])[CH2:26][Br:9])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 86618355HCID 86618355, compound

Product 1

HCID 86618356HCID 86618356, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (0.95 g, 5.3 mmol) and a drop of hydrobromic acid were added to a solution of ethyl 2-benzoyl-4-bromo-4-pentenoate (1.5 g, 4.82 mmol) in acetonitrile (16 ml) and water (4 ml), followed by stirring at room temperature for 3 hours and 40 minutes. The reaction mixture was diluted with diethyl ether, and a 5% aqueous sodium thiosulfate solution was added to separate the mixture into layers. The organic layer was washed twice with a saturated aqueous sodium hydrogencarbonate solution, washed with a saturated salt solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1). The solvent was distilled off under reduced pressure, to thereby obtain 0.91 g (yield: 58%) of ethyl 2-benzoyl-5-bromo-4-oxopentenoate as a colorless oil.

Workup

  1. customto separate the mixture into layers
  2. washThe organic layer was washed twice with a saturated aqueous sodium hydrogencarbonate solution
  3. washwashed with a saturated salt solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5abe242717f04ad9b3dc2ef67ce13453
Source dataset
uspto-grants-2010_02
Patent number
US07655680B2

Reaction notes

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