Ethyl 2-methylacetoacetate → HCID 12382131, compound

HRID 1848428Notes

Reaction equation

HRID 1848428 reaction equation
[CH3:1][CH:2]([C:8](=[O:10])[CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:11]Br>O>[Br:11][CH2:9][C:8](=[O:10])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 24408Bromine

Product 1

HCID 12382131HCID 12382131, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-methyl-3-oxobutanoate (5.05 g, 35.0 mmol) in water (10 mL) at 0° C. was added bromine (1.81 mL, 35.0 mmol) dropwise over 2 h. The resulting solution was stirred at rt for 16 h. The reaction mixture was extracted with ethyl acetate, the organic phase was dried over sodium sulfate and concentrated to give ethyl 4-bromo-2-methyl-3-oxobutanoate. 1HNMR (500 MHz, CDCl3), δ4.322-4.274 (m, 2H), 2.455 (s, 2H), 1.991 (s, 3H), 1.337-1.309 (t, 3H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-47d9ae0d95414d3fa6b2a9b2e9d548c7
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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