Bromine → HCID 15758244, compound

HRID 1848451Notes

Reaction equation

HRID 1848451 reaction equation
[CH2:1]([CH:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Br:12]Br>O>[Br:12][CH2:10][C:9](=[O:11])[CH:3]([CH2:1][CH3:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl ester

Product 1

HCID 15758244HCID 15758244, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 2-ethyl-3-oxobutanoate (5.17 g, 32.7 mmol) in water (10 mL) at 0° C. was added bromine (1.684 mL, 32.7 mmol) dropwise over 2 h. The resulting solution was stirred at rt for 16 h. The mixture was extracted with ethyl acetate (100 mL) and the organic phase was dried over sodium sulfate and concentrated to give ethyl 4-bromo-2-ethyl-3-oxobutanoate. 1HNMR (500 MHz, CDCl3), δ4.327-4.284 (m, 2H), 2.412 (s, 2H), 2.320-2.212 (q, 2H), 1.338-10309 (m, 3H), 1.042-1.013 (t, J=7.3 Hz, 3H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (100 mL)
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2ac47b5e22884d7988fcb8eb2a93dc86
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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