Bromine → Ethyl 3-bromo-4-oxobutanoate

HRID 383111

Reaction equation

HRID 383111 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH:7]=[O:8])[CH3:2].[Br:10]Br>C(OCC)C>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH:6]([Br:10])[CH:7]=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 82395Ethyl 4-oxobutanoate

Product 1

HCID 15576269Ethyl 3-bromo-4-oxobutanoateYield 66.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 0-5° C. mechanically-stirred solution in diethyl ether (100 mL) of succinaldehydic acid ethyl ester (10.0 g, 77 mmol) was added bromine (3.9 g, 151 mmol) over 2.5 hours. The reaction mixture was stirred for an additional 1.25 hours and the ether was distilled at atmospheric pressure. The remaining yellow oil was distilled (6.0-6.5 mm Hg, bp 95-101° C.) to give 3-bromosuccinaldehydic acid ethyl ester (10.7 g, 66%).

Workup

  1. distillationthe ether was distilled at atmospheric pressure
  2. distillationThe remaining yellow oil was distilled (6.0-6.5 mm Hg, bp 95-101° C.)

Sources & evidence

ORD record
ord-e27d267f52fb48c582371c116a9045d5
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Linked notes

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