Magnesium perchlorate → 2-Bromo-3-oxo-hexanoic acid ethyl ester

HRID 401597

Reaction equation

HRID 401597 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[CH3:2].Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[Br:23]N1C(=O)CCC1=O>C(OCC)(=O)C.C(OCC)C>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([Br:23])[C:6](=[O:10])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

6

Reactant 3

HCID 24840Magnesium perchlorateHCID 67184N-bromobutanimideHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 130155942-Bromo-3-oxo-hexanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3-Oxo-hexanoic acid ethyl ester (4.0 mL, 25 mmol) and magnesium perchlorate (1.7 g, 7.6 mmol) were placed in 500 mL of ethyl acetate and allowed to stir for 5 minutes. N-Bromosuccinimide (4.7 g, 26 mmol) was added and the reaction mixture was allowed to stir for 15 minutes, at which time thin-layer chromatography (10% ethyl acetate in hexanes, silica gel, 254 nm irradiation) indicated the reaction was complete. The reaction mixture was diluted with 500 mL of ethyl ether and washed three times with an equal volume of saturated aqueous sodium chloride. The organic layer was then dried over sodium sulfate and evaporated to dryness. This material was used in the next step without further purification.

Workup

  1. washwashed three times with an equal volume of saturated aqueous sodium chloride
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. customevaporated to dryness
  4. customThis material was used in the next step without further purification

Sources & evidence

ORD record
ord-e9222980ba39455cb6073d6bb32e4d1b
Source dataset
uspto-grants-2014_06
Patent number
US08741939B2

Linked notes

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