N-bromobutanimide → HCID 90408806, compound

Participants

Reaction Conditions

Reaction Steps

To a solution or methyl 2-fluoro-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0.6 g, 2.040 mmol) in 40 ml CCl4 was added N-Bromosuccinimide (0.363 g, 2.040 mmol) and (E)-1,1′-(diazene-1,2-diyl)dicyclohexanecarbonitrile (0.050 g, 0.204 mmol). The mixture was stirred at 80° C. overnight. The reaction mixture was extracted with 5% KOH in water (3×20 ml). The water phase stirred for 1 hour and then the solution was cooled to 0° C. and slowly acidified to pH<1 with 1N HCl. The precipitant that formed was filtered onto fritted filter and dried in vacuum for overnight to give 0.137 g of IXS-5-49-1, 1H NMR in DMSO-d6 is consistent with desired product. MS [MH+]=196.

Provenance & Evidence