Synthesis of 3-bromo-3-phenylpropanoic acid

Preparation of 3-bromo-3-phenylpropanoic acid

10 g of finely powdered cinnamic acid are shaken for two days with 50 ml of an aqueous solution of hydrobromic acid saturated with the gas at 0° C. The 3-bromo-3-phenylpropanoic acid precipitate is collected, washed with a little ice-water and dried in vacuum over.

A more advanced method for preparation of 3-bromo-3-phenylpropanoic acid is to saturate glacial acetic acid at room temperature with hydrobromic acid (1 part of glacial acetic acid dissolves about 0.6 part of HBr), and then to heat the obtained solution with the cinnamic acid at 100° C for two hours. On cooling, the 3-bromo-3-phenylpropanoic acid crystallizes out. The product is very readily decomposed by water and it can only be recrystallized from anhydrous solvents. 3-bromo-3-phenylpropanoic acid is slightly soluble in dry carbon disulfide in the cold, whereas cinnamic acid itself is readily dissolved. Purified by crystallization product is colorless crystals has melting point 137° C.

Preparation of organic compounds, E. de. Barry Barnett, 63, 1912

By slightly modified method 10 g of finely powdered cinnamic acid are heated in a sealed tube  for 2 hours at 100° C with 10 g of glacial acetic acid which has been saturated with hydrogen bromide at ordinary temperature. (1 g of glacial acetic acid dissolves about 0.6 g of hydrogen bromide, so there is an excess of the latter present.) The precipitate is recrystallized from dry carbon disulfide (the acid is readily decomposed by water) in which cinnamic acid is readily soluble, even in the cold. 3-Bromo-3-phenylpropanoic acid forms colourless crystals; soluble in hot, slightly soluble in cold carbon disufhide; m.p. 137 ° C.

Systematic organic chemistry, by W. M. Cumming, 340-341, 1937.

IUPAC Name

3-bromo-3-phenylpropanoic acid

InChI

InChI=1S/C9H9BrO2/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)

InChI Key

JQRMHJWFYKSDNQ-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

3-Bromo-3-phenylpropanoic acid, .beta.-Bromohydrocinnamic acid, Benzenepropanoic acid, .beta.-bromo-, b-bromobenzenepropanoic acid, 15463-91-9, 3-Bromo-3-phenylpropionic acid, JQRMHJWFYKSDNQ-UHFFFAOYSA-N, Hydrocinnamic acid, .beta.-bromo-, SBB008428, beta-Bromohydrocinnamic acid, AC1L5EJ3, SCHEMBL777871, AC1Q249F, 3-BROMOPHENYLPROPANOICACID, MolPort-002-501-931, 3-Bromo-3-phenylpropanoic acid #, NSC16255, AR-1H7788, NSC-16255, AKOS022506669, FR-2037, MCULE-7295763261, KB-181097, FT-0622596, 3B3-049264

Removed Synonyms

CID226117, 19062-51-2

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