Furfural → 2-Bromo-1-(2-furyl)-2-nitroethanol

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The use of 2-(2-Bromo-2-nitroethenyl)furan as an antimicrobial with a broad spectrum of uses in water treatment, pulp and paper manufacturing, metal working fluids and various non-oxidizing biocide applications has been described. One process for producing BNEF comprises the reaction of furfural with bromonitromethane using a primary amine or primary amine salt and sodium carbonate as the catalytic agent at 10 mol% to produce an intermediate 2-Bromo-1-(2-furyl)-2-nitroethanol, which is dehydrated in the presence of acid to the desired product. The preferred solvent is ethanol. In a typical procedure, the reaction mixture is stirred for 25 hours at 5° C., and the acid is then added to effect the dehydration. The reaction mixture is extracted with methylene chloride and the crude product recovered as an oil which is steam-distilled. The solid product is filtered from the steam-distillate and recrystallized from ethanol, and the yield is reported to be in the range of 23%.

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