4-(Bromomethyl)-3-fluorobenzoicacid synthesis

5synthesis methods

Product Name:4-(Bromomethyl)-3-fluorobenzoicacid
CAS Number:361456-46-4
Molecular formula:C8H6BrFO2
Molecular Weight:233.03

350-28-7 Synthesis

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361456-46-4
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Yield:361456-46-4 30%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in chloroform;Reflux;Inert atmosphere;

Steps:

4-(bromomethyl)-3-fluorobenzoic acid

A suspension of 3-fluoro-4-methyl-benzoic acid (7 g, 45.4 mmol) and l-bromopyrrolidine-2,5-dione (8.08 g, 45.4 mmol) in CHCI3 (150 mL) was heated to reflux until a homogeneous solution was achieved. To the reaction was added AIBN (100 mg, 0.61 mmol) and the resulting mixture stirred at reflux overnight. The reaction was cooled to rt and concentrated in vacuo, to give an orange solid. The material was triturated with a mixture of DCM (50 mL) and isohexane (50 mL) and the by-product filtered off. The filtrate was concentrated in vacuo and purified by column chromatography eluting with isohexane in EtOAc (0-100%). The title compound (5.22 g, 13.4 mmol, 30% yield) was isolated as a white solid. (0442) [M+HC0₂H]⁺ = 277.1/291.1

References:

WO2019/106359,2019,A1 Location in patent:Page/Page column 39; 33

51436-99-8 Synthesis