N-bromobutanimide → 1-(Bromomethyl)-3-methanesulfonylbenzene

Participants

Reaction Steps

A solution of 1.0 g of 3-methanesulphonyltoluene in 5.9 ml of tetrachloromethane was admixed with 1.05 g of N-bromosuccinimide 11.8 mg of 2,2′-azoisobutyronitrile at 25° C. and subsequently refluxed for 5 hours. After decanting the orange precipitate was washed with tetrachloromethane and the combined organic phases were concentrated under reduced pressure. The 3-bromomethylphenyl methyl sulphone thus obtained was used in the next stage without further clarification. 100 mg of (E/Z)-N′-(4-bromo-2-cyano-5-hydroxyphenyl)-N,N-dimethylformimidamide are suspended in 1.5 ml of acetone together with the bromide freshly prepared above and after admixture of 95.4 mg of potassium carbonate refluxed for 3 hours. After cooling to 25° C., the reaction mixture was admixed with 25 ml of water and washed twice with 25 ml of ethyl acetate each time. The combined organic phases were washed with 25 ml of saturated sodium chloride solution, dried over sodium sulphate and, after filtration, concentrated under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel with ethyl acetate to obtain 166 mg of (E/Z)-N′-[2-Cyano-5-(3-methanesulphonylbenzyloxy)-4-bromophenyl]-N,N-dimethylformamidine.

Provenance & Evidence