Bromomethyl Substituted compounds

Halomethyl derivatives have been proved to be valuable intermediates for the preparation of catalysts and active substances, for example plant protection agents, dyes and polymers to pharmaceuticals. Among them, bromomethyl aromatics are a particular class, due to its higher reactivity than chloromethyl aromatics. Bromomethyl aromatics are not only more easily converted into alcohols, aldehydes, amine, carboxylic acids, esters, acrylic and metal organic compounds, but also very useful for some of difficult synthesis reactions with chloromethyl aromatics. Consequently, a sustained interest has been focused on the bromomethylated aromatics preparation. In general, bromomethyl compounds can be prepared either from a direct bromination of the corresponding aromatic methyl compounds, or from a deoxybromination of benzylic alcohol.


  Synthesis of Bromomethyl Substituted compounds



Methyl 3-methyl-benzoate (15.0 g, 0.1 mol) was dissolved in 150 mL carbon tetrachloride and N-bromosuccinimide (20.0 g, 0.11 mol) was added. The mixture was refluxed for 6 h accompanied with illumination and the white succinimide residue was filtered off. The solvent was evaporated under reduced pressure to give a yellow liquid, which was purified with ether at -78 deg C to get 4a as a yellow liquid at room temperature (21.6 g, 94.3% yield).


Phosphorous tribromide (2.04 g, 7.52 mmol) was added to a stirred solution of 2-methoxybenzyl alcohol (3.00 g, 21.5 mmol) and toluene (25 mL) at 40 deg C. The solution was heated to 100 deg C for 10 min, and the reaction was cooled to ambient temperature. The liquid was decanted and washed with water (2 X 50 mL) and brine (50 mL). The combined aqueous washes were extracted with ether (75 mL), and the combined organic fractions were spin evaporated to give 4.9 g of a semisolid residue. The residue was dissolved in ether (100 mL) and washed with water (2 X 50 mL) and brine (50 mL). The organic phase was spin evaporated to an oil, which was repeatedly coevaporated with toluene to give 4.04 g (94%) of 2-methoxybenzyl bromide as a golden oil.


To a solution of I01-5816 (2.0 g, 9.3 mmol, 1.0 equiv) in CH2Cl2 (60 mL) at 0 °C was added PPh3 (3.67 g, 14.0 mmol, 1.5 equiv) and CBr4 (4.64 g, 14.0 mmol, 1.5 equiv). After 30 min the reaction was concentrated in-vacuo, then the residue was taken up in Et2O (50 mL) and placed at -20 °C for 30 min. The solution was filtered to remove solid Ph3PO and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (hexanes/EtOAc) afforded the title compound (2.28 g, 88%).


The application of Bromomethyl Substituted compounds


    Tetrahedron Lett.,2011, 1574 â€?1577


    Eur. J. Med. Chem.,2011,1207 â€?1221


    Bioorg. Med. Chem.,2009, 17,1307-1324


    J. Chem. Soc. 1951, 2430-2440



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