N-bromobutanimide → Dibenzyl bromopropanedioate

HRID 2282207Notes

Reaction equation

HRID 2282207 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].C([O-])(=O)C.[NH4+].[Br:27]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>C(OCC)C.C(OCC)(=O)C>[Br:27][CH:2]([C:1]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

7

Reactant 4

HCID 67184N-bromobutanimideHCID 84754Dibenzyl malonateHCID 516892Sodium BicarbonateHCID 517165Ammonium Acetate

Product 1

HCID 15178112Dibenzyl bromopropanedioateYield 29.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of dibenzyl malonate (10.0 g, 35.0 mmol) in diethyl ether (20 mL) were added ammonium acetate (270 mg, 3.5 mmol) and N-bromosuccinimide (6.9 g, 39 mmol), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) were added to the reaction solution, and the mixture was stirred for 30 min. The organic layer was washed with saturated aqueous potassium carbonate solution (100 mL) and saturated brine (10 mL) and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→50/50) to give the title compound (3.8 g, 29%) as a brown oil.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with saturated aqueous potassium carbonate solution (100 mL) and saturated brine (10 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe insoluble material was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→50/50)

Sources & evidence

ORD record
ord-7860147a01144291aa25e82c0cb8170d
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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