Boron tribromide → HCID 22921546, compound

Participants

Reaction Conditions

Reaction Steps

One hundred mL of methylene chloride was stirred and cooled to about -40° C. To this was added dropwise 11.0 mL (0.011 mole) of boron tribromide (1.0M in methylene chloride). Upon completion of the addition, the reaction mixture was again cooled to -40° C., and a solution of 4.5 grams (0.010 mole) of 1-methyl-3-(1-methoxymethylethyl-2-trifluoromethyl-5-fluorobenzimidazol-6-yl)-6-trifluoromethyluracil (Compound 8--prepared in a manner analogous to that of Example 3) in about 20 mL of methylene chloride was added dropwise. Upon completion of the addition, the reaction mixture was stirred for an additional one hour at -40° C. After this time the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours. The reaction mixture was then poured into a flask, and ice was added. The mixture was stirred until the ice melted, and then extracted with ethyl acetate. The combined extracts were washed with an aqueous solution saturated with sodium chloride and dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure, yielding 4.3 grams of 2-[2-trifluoromethyl-5-fluoro-6-(1-methyl-6-trifluoromethyluracil-3-yl)benzimidazol-1-yl]propan-1-ol. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence