Bromine → Methyl 4-bromo-5-oxo-5-phenylpentanoate

HRID 1295213Notes

Reaction equation

HRID 1295213 reaction equation
[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[Br:16]Br.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)C>[Br:16][CH:3]([C:2](=[O:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 137042Methyl 4-benzoylbutyrate

Product 1

HCID 11066004Methyl 4-bromo-5-oxo-5-phenylpentanoateYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 5-oxo-5-phenylpentanoate (16.1 g) in diethyl ether (100 ml) was added bromine (4.01 ml) at room temperature over 30 min. and the mixture was stirred for 30 min. An aqueous sodium sulfite solution was added to the reaction mixture and the mixture was extracted with diethyl ether. The diethyl ether layer was washed with saturated brine, dried (MgSO4) and concentrated to give methyl 4-bromo-5-oxo-5-phenylpentanoate (22.1 g, yield 100%) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe diethyl ether layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2c393139b8b041809e1de76f979495b7
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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