Ethyl 2-methylacetoacetate → HCID 12382131, compound

HRID 1501746Notes

Reaction equation

HRID 1501746 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-ddd9d5f0375844978708113bd83b361d
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

Loading…