Ethyl benzoylacetate → ethyl 2-bromo-3-oxo-3-phenylpropanoate

HRID 589031Notes

Reaction equation

HRID 589031 reaction equation
[C:1]([CH2:9][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.[Br:15]N1C(=O)CCC1=O.CCOC(C)=O>CS(C)=O>[Br:15][CH:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 8857Ethyl AcetateHCID 67184N-bromobutanimide

Product 1

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoateYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl benzoylacetate (0.27 mL, 1.6 mmol) [Fluka cat#12990] was dissolved in dimethyl sulfoxide (5.0 mL) at room temperature and the N-bromosuccinimide (0.30 g, 1.7 mmol) was added portion wise. The reaction mixture was stirred for 3 h and EtOAc was added and washed with water, water saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give Ethyl 2-bromo-3-oxo-3-phenylpropanoate (0.40 g, 95%) as an oil %). LCMS calc. for C11H12BrO3 (M+H)+: m/z=271.0, 273.0. found: 271.0, 273.0.

Workup

  1. washwashed with water, water saturated sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9985f1e005bd428d82c4b1b3df77c8f4
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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