Sodium hydride → HCID 118093886, compound

Participants

Reaction Steps

A solution of cyclopropyl carbinol (0.269 mL, 3.40 mmol) in tetrahydrofuran (6.9 mL) at 0° C. was treated with sodium hydride (0.0860 g, 3.40 mmol) and stirred at RT for 30 min. The reaction mixture was cooled to 0° C., treated with 4-bromo-3-fluoro-2-nitroaniline (0.400 g, 1.70 mmol) [Combi-Blocks, AN-2785] and stirred at RT for 15 h. The reaction mixture was cooled to 0° C. and quenched with saturated ammonium chloride solution. The reaction mixture was diluted with ethyl acetate (50 mL) and water (40 mL). The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated to give crude oil. Purification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes) gave the desired product (0.365 g, 75%). LCMS calculated for C10H12BrN2O3 (M+H)+: m/z=287.1. found: 286.8.

Provenance & Evidence