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ChemicalBook CAS DataBase List 4-Bromomethylbenzoic acid
6232-88-8

4-Bromomethylbenzoic acid synthesis

12synthesis methods
p-Toluic acid

99-94-5

4-Bromomethylbenzoic acid

6232-88-8

In a 100 mL round-bottomed flask, 40 mL of carbon tetrachloride was added as solvent, 3.00 g of p-methylbenzoic acid as starting material, 4.00 g of N-bromosuccinimide (NBS) as bromination reagent, and 0.1 g of azobisisobutyronitrile (AIBN) as initiator. The reaction mixture was stirred and refluxed at 90 °C and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature followed by filtration. The filter cake was washed with warm water to remove the succinimide by-products generated in the reaction. After drying, 4.02 g of p-bromomethylbenzoic acid was obtained with a melting point of 231-232°C in 84% yield.

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Yield:6232-88-8 90%

Reaction Conditions:

with sodium bromate;sodium hydrogensulfite in water;ethyl acetate

Steps:

1.1 Step 1
p-Toluic acid was treated with sodium bromate and sodium bisulfite in ethyl acetate and water to obtain p-bromomethylbenzoic acid in 90% yield (step 1).

References:

CHANNEL THERAPEUTICS, INC.;RAMANUJACHARY, Kandalam, V.;SUMAN, Pathi;PEREZ, Lark, J.;JONNALAGADDA, Subash, C. WO2019/60809, 2019, A1 Location in patent:Paragraph 0125

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