ChemicalBook CAS DataBase List 2-BROMOOCTANOIC ACID

2-BROMOOCTANOIC ACID synthesis

6synthesis methods

Product Name:2-BROMOOCTANOIC ACID
CAS Number:2623-82-7
Molecular formula:C8H15BrO2
Molecular Weight:223.11

124-07-2 Synthesis

124-07-2
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2623-82-7
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$60.00/500mg

Yield:2623-82-7 67%

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]