ChemicalBook CAS DataBase List A-BROMOHEPTANOIC ACID

A-BROMOHEPTANOIC ACID synthesis

5synthesis methods

Product Name:A-BROMOHEPTANOIC ACID
CAS Number:2624-01-3
Molecular formula:C7H13BrO2
Molecular Weight:209.08

111-14-8 Synthesis

111-14-8
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2624-01-3
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Yield:2624-01-3 69%

Reaction Conditions:

with thionyl chloride;bromine;sodium hydroxide at 20;Reflux;Hell-Volhardt-Zelinski Bromination;

Steps:

Synthesis of α-brominated fatty acids 5b-f

General procedure: To a flask equipped with a sodium hydroxide trap the corresponding fatty acid 4 (0.065 mol) and thionyl chloride (5 equiv,40 mL, 0.325 mol) were added. The reaction mixture was stirred at 50 °C in a water bath. Then, liquid bromine (3 equiv,5 mL, 0.195 mol) was added dropwise and the reaction mixture was stirred under reflux for 6 h and then at room temperature overnight. The excess of thionyl chloride was then removed by distillation. To a beaker containing distilled water in an ice bath,the dark red residue was slowly added and manually stirred.Afterwards, the solution was heated and subsequently cooled,resulting in the precipitation of a pale yellow solid for the longer chain fatty acids which was decanted, washed with distilled water, and once again submitted to the crystallization procedure.

References:

Syrpas, Michail;Ruysbergh, Ewout;Stevens, Christian V.;De Kimpe, Norbert;Mangelinckx, Sven [Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 2539 - 2549]