N-bromobutanimide → Diethyl dioxobutanedioate

HRID 1028476Notes

Reaction equation

HRID 1028476 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]([C@H:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[OH:8])[OH:6])[CH3:2].BrN1C(=O)CCC1=O.N(C(C)(CC(OC)(C)C)C#N)=NC(C)(CC(C)(OC)C)C#N>C(O)(=O)C>[O:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])[C:7](=[O:8])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 858672,2'-Azobis(2,4-dimethyl-4-methoxyvaleronitrile)HCID 6993580Diethyl tartrate

Product 1

HCID 263091Diethyl dioxobutanedioate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

L-Tartaric acid diethyl ester (10.0 g), acetic acid (100 ml), N-bromosuccinimide (34.5 g) and 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (0.15 g) were mixed, and the reaction solution was stirred at 55° C. for 3 hours. The reaction solution was concentrated under reduced pressure until its volume became 50 ml to afford a solution of diethyl dioxobutanedioate in acetic acid as a yellow liquid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure until its volume

Sources & evidence

ORD record
ord-4b01cc2b5ebf498da1ed9393ac0462fe
Source dataset
uspto-grants-2014_05
Patent number
US08735598B2

Reaction notes

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