Fumarate → bromomesaconic acid

HRID 1589333Notes

Reaction equation

HRID 1589333 reaction equation
[Br:1][CH2:2]/[C:3](=[CH:7]/[C:8]([OH:10])=[O:9])/[C:4]([OH:6])=[O:5].C([O-])(=O)/C=C/C([O-])=O.BrCC1C(OC(=O)C=1)=O>>[Br:1][CH2:2]/[C:3](=[CH:7]\[C:8]([OH:10])=[O:9])/[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 5460307FumarateHCID 109870762,5-Furandione, 3-(bromomethyl)-HCID 86740308HCID 86740308, compound2×

Product 1

HCID 6449799bromomesaconic acid

Procedure

Steps are taken to avoid isomerization of 2-(bromomethyl)-maleic acid (3) to the corresponding fumarate analog by hydrolyzing the anhydride (2) in a dilute aqueous solution and neutralizing the diacid (3) immediately after complete hydrolysis. Any bromomethyl fumaric acid derivative formed is removed in purifying compound (4) as described in more detail below.

Workup

  1. customimmediately after complete hydrolysis

Sources & evidence

ORD record
ord-175c0a18416848a2975bcd98424f1b90
Source dataset
uspto-grants-1986_02
Patent number
US04569789

Reaction notes

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