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ChemicalBook CAS DataBase List 4-Bromo-2-(bromomethyl)-1-iodobenzene
495414-06-7

4-Bromo-2-(bromomethyl)-1-iodobenzene synthesis

3synthesis methods
-

Yield: 50%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethaneReflux;

Steps:


A mixture of 5-bromo-2-iodotoluene (25.0g, 0.1mol), NBS (36.6g, 0.1mol), and BPO (0.6g, 2.6mmol) were dissolved in 200mL of CCl4 and refluxed. The mixture was allowed to stir until the completion of the reaction, which was confirmed by thin layer chromatography (TLC) analysis (7h). When the reaction ended, a large amount of the floating succinimide produced in the reaction systems was filtrated off. The filtrate was evaporated to remove the solvent. The crude product was purified by column chromatography on silica with petroleum ether as the eluent to give 16.3g of a white solid 5-bromo-2-iodobenzyl bromide. Yield:50%; 1H NMR (600MHz, CDCl3): δ=4.52 (s, 2H, Ph-CH2), 7.21-7.59(m, 3H, Ar-H) ppm.

References:

Guan;Jia;Zhang;Zhang;Ma;Lu;Lai;Lei [Dyes and Pigments,2017,vol. 136,p. 873 - 880]

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