N-bromobutanimide → HCID 22050959, compound

Participants

Reaction Steps

A 100 mL round bottomed flask equipped with stirbar and nitrogen inlet was charged with the product of Step 3 (2.1 g, 5.06 mmol) and N methyl 2-pyrrolidine (10 mL). N-Bromo succinimide (1 g, 5.56 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The mixture poured into saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried with Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica (1:1 hexanes; ethyl acetate) to give the title compound as an orange oil (0.77 g, 31%). 1H NMR (400 MHz, CD3OD) δ 8.16 (app qd, J=2.5 and 7.2 Hz, 1H), 7.84 (d, J=2.6 Hz, 1H), 7.64 (m, 1H), 7.30 (d, J=9.2 Hz, 1H), 7.04 (appt, J=8.4 Hz, 2H), 6.60 (s, 1H), 5.33 (s, 2H), 3.80 (s, 6H), 1.99 (s, 3H) ppm. 19F NMR (400 MHz, CD3OD) δ −111.56 (1F), −116.00 (1F) ppm. ES-HRMS m/z 494.0398 (M+H calcd for C22H13BrF2NO5 requires 494.0409).

Provenance & Evidence