Synthesis of 2,3-dibromo-3-phenylpropanoic acid

Preparation of 2,3-dibromo-3-phenylpropanoic acid

2,3-dibromo-3-phenylpropanoic acid is prepared by reacting bromine with cinnamic acid

To the round bottom flask fitted with dropping funnel 25 g of cinnamic acid are dissolved in 100-125 ml of dry ether are placed. The reaction flask is cooled with ice-water and 27 g of bromine are then slowly added, and, as the reaction is very violent in direct sunlight, care must be taken to exclude all but diffused light. When all the bromine has been added, the reaction solution becomes colorless. The ether is removed by evaporation and residue is crystallized from dilute ethyl alcohol. Instead of evaporating the ether, the 2,3-dibromo-3-phenylpropanoic acid can be extracted by shaking out with dilute solution of sodium hydroxide in order to form sodium salt, and then precipitated from the aqueous extract by acidifying with hydrochloric acid. 2,3-dibromo-3-phenylpropanoic acid is colorless leaflets with melting point 195° C. Yield is obtained almost quantitative.

Preparation of organic compounds, E. de. Barry Barnett, 62, 1912

By slightly modified method 40 g of finely divided cinnamic acid are spread out on a large clock-glass and placed in a desiccator over concentrated sulfuric acid. A dish containing 45 g of dry bromine is supported on a glass tripod above the cinnamic acid, the desiccator is closed, and allowed to stand until all the bromine has evaporated from the dish, and has been absorbed by the acid (about 3 days). The clock-glass is removed, the product exposed to the air for several hours, weighed in order to make sure that the theoretical amount of bromine has been absorbed, and recrystallized from dilute alcohol. The yield theoretical (90 g.). Colourless leaflets; m.p. 195 °C (decomposition).

Systematic organic chemistry, by W. M. Cumming, 340, 1937.

IUPAC Name

2,3-dibromo-3-phenylpropanoic acid

InChI

InChI=1S/C9H8Br2O2/c10-7(8(11)9(12)13)6-4-2-1-3-5-6/h1-5,7-8H,(H,12,13)

InChI Key

FXJWTHBNVZNQQP-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C(C(=O)O)Br)Br

Depositor-Supplied Synonyms

2,3-Dibromo-3-phenylpropanoic acid, 2,3-Dibromo-3-phenylpropionic acid, alpha,beta-Dibromohydrocinnamic acid, 6286-30-2, 2,3-Dibromohydrocinnamic acid, Propionic acid, 2,3-dibromo-3-phenyl-, .alpha.,.beta.-Dibromohydrocinnamic acid, EINECS 228-516-3, NSC 10049, alpha,beta-Dibromobenzenepropanoic acid, BRN 2050283, AI3-18459, HYDROCINNAMIC ACID, alpha,beta-DIBROMO-, AC1L2KWT, a b-dibromohydrocinnamic acid, a,b-dibromohydrocinnamic acid, SCHEMBL511309, ACMC-209n99, 168440_ALDRICH, AC1Q71N5, CTK5I5764, FXJWTHBNVZNQQP-UHFFFAOYSA-N, MolPort-000-153-881, Hydrocinnamic acid,.beta.-dibromo-, NSC10049, 2 3-dibromo-3-phenylpropionic acid, ANW-34411, NSC-10049, NSC176177, SBB007805, STK286095, Benzenepropanoic acid,.beta.-dibromo-, AKOS001482347, AKOS016038176, FR-0373, MCULE-2104980401, NSC-176177, LS-77166, 2,3-DIBROMO-3-PHENYLPROPIONICACID, Benzenepropanoic acid, alpha,beta-dibromo-, KB-163992, TR-021627, 4043P, D2647, EU-0033643, FT-0609515, Hydrocinnamic acid, .alpha.,.beta.-dibromo-, Benzenepropanoic acid, .alpha.,.beta.-dibromo-, 2-09-00-00344 (Beilstein Handbook Reference), Benzenepropanoic acid, alpha,beta-dibromo- (9CI), I04-8838, 3B3-029246, 31357-31-0

Removed Synonyms

, -Dibromohydrocinnamic acid, CID22705

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *