Bromine → Ethyl 2-bromo-4-methyl-3-oxopentanoate

HRID 2059646Notes

Reaction equation

HRID 2059646 reaction equation
C([O-])(=O)C.[Na+].[CH2:6]([O:8][C:9](=[O:16])[CH2:10][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])[CH3:7].[Br:17]Br>C(O)(=O)C>[Br:17][CH:10]([C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])[C:9]([O:8][CH2:6][CH3:7])=[O:16]

Participants

5

Reactant 3

HCID 24408BromineHCID 81583Ethyl isobutyrylacetateHCID 517045Sodium Acetate

Product 1

HCID 13015595Ethyl 2-bromo-4-methyl-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of sodium acetate (1.9 g) in glacial acetic acid (15 ml) was added 4-methyl-3-oxo-pentanoic acid ethyl ester (2 g) and the reaction mixture cooled to 10° C. Bromine (0.7 ml) was then added dropwise. The resulting solution was allowed to warm to room temperature and stirred for 1 h. The reaction was complete (by TLC) and was concentrated in vacuum affording 3.8 g crude ethyl product which was used directly in the next synthetic step.

Workup

  1. temperatureto warm to room temperature
  2. concentrationwas concentrated in vacuum
  3. customaffording 3.8 g crude ethyl product which

Sources & evidence

ORD record
ord-759e2a9e251847ada9516c7bb45b89cd
Source dataset
uspto-grants-2012_10
Patent number
US08278302B2

Reaction notes

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