Synthesis of bromosuccinic acid

Preparation of bromosuccinic acid

Preparation of bromosuccinic acid

Preparation of bromosuccinic acid

To the round bottom flask fitted with dropping funnel and reflux condenser a mixture of 18 g of dry succinic acid and 3-5 g of red phosphorus are placed. The top end of the condenser is connected with an absorption flask for the hydrobromic acid and bromine fumes. From the dropping funnel 80 g of bromine are added slowly to the reaction flask. During the addition of bromine a very violent reaction takes place, which is controlled by the rate of addition of bromine. When all the bromine has been added the reaction mixture is heated until the bromine has disappeared. The reaction content is poured slowly into 100 ml of boiling water. When all the reaction mixture has been added, the solution is filtered, cooled, and repeatedly extracted with ethyl ether. Ethereal extracts are combined and evaporated, and the solid residue of bromosuccinic acid recrystallized from a small amount of water yielding 80-90 %. Bromosuccinic acid melts at 160° C.

Preparation of organic compounds, E. de. Barry Barnett, 57, 1912

IUPAC Name

2-bromobutanedioic acid

InChI

InChI=1S/C4H5BrO4/c5-2(4(8)9)1-3(6)7/h2H,1H2,(H,6,7)(H,8,9)

InChI Key

QQWGVQWAEANRTK-UHFFFAOYSA-N

Canonical SMILES

C(C(C(=O)O)Br)C(=O)O

MeSH Synonyms

bromosuccinate, bromosuccinic acid, bromosuccinic acid, (+-)-isomer

Depositor-Supplied Synonyms

Bromosuccinic acid, 2-bromobutanedioic acid, 2-Bromosuccinic acid, Monobromosuccinic acid, 923-06-8, Butanedioic acid, bromo-, Bromobutanedioic acid, Succinic acid, bromo-, QQWGVQWAEANRTK-UHFFFAOYSA-N, NSC 227872, ST51037536, DL-bromosuccinic acid, (S)-(-)-Bromosuccinicacid, RS-bromosuccinic acid, (+-)-bromosuccinic acid, ACMC-1ARR3, AC1L2K2V, L-2-bromosuccinic acid, 4, 2-bromo-2-deoxy-malic acid, B81204_ALDRICH, SCHEMBL180137, AC1Q243M, Succinic acid, bromo- (8CI), CHEBI:73712, CTK3I9727, QQWGVQWAEANRTK-UHFFFAOYSA-, Butanedioic acid, bromo- (9CI), MolPort-001-792-864, EINECS 213-087-7, AR-1D9740, NSC227872, STL280260, AKOS005208711, AN-9907, MCULE-8178780603, NSC-227872, RTR-032074, Butanedioic acid, bromo-, (.+/-.)-, AK-43673, S343, AI3-52316, DB-057296, TR-032074, A4536, FT-0633099, I01-2276, I14-19996, 3B3-001164, 3B3-029250, InChI=1/C4H5BrO4/c5-2(4(8)9)1-3(6)7/h2H,1H2,(H,6,7)(H,8,9)

Removed Synonyms

(S)-2-bromosuccinic acid, (S)-(-)-2-Bromosuccinic acid, CID73557, 20859-23-8, 98088-95-0

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