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

HRID 1848464Notes

Reaction equation

HRID 1848464 reaction equation
[CH3:1][CH:2]([C:8](=[O:11])[CH2:9][CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][CH:9]([CH3:10])[C:8](=[O:11])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 24408BromineHCID 231471Pentanoic acid, 2-methyl-3-oxo-, ethyl ester

Product 1

HCID 15758245Ethyl 4-bromo-2-methyl-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of ethyl 2-methyl-3-oxopentanoate (5.0 g, 34.7 mmol) in chloroform at 0° C. was added bromine (1.79 mL, 34.7 mmol) in chloroform (10 mL) drop-wise. The resulting solution was stirred at rt for 16 h. The solution was washed with water, dried over sodium sulfate, and concentrated to give the title compound. 1HNMR (500 MHz, CDCl3), δ4.781-4.740 (dd, J=6.6 Hz, 1H), 4.140-4.098 (dd, J=7.0 Hz, 1H), 3.770 (s, 3H), 1.797-1.783 (d, J=6.6 Hz, 3H), 1.455-1.442 (d, J=7.0 Hz, 3H).

Workup

  1. washThe solution was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3889e3e371bb486f93520d2325586edc
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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