N-bromobutanimide → HCID 66823682, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 4-fluoro-2,3-dihydro-1H-indole-1-carboxylate (0.866 g, 3.65 mmol) in Dichloromethane (DCM) (10 mL) was added a solution of NBS (0.650 g, 3.65 mmol) in Dichloromethane (DCM) (10 mL). The reaction was stirred overnight. The reaction mixture was poured into sodium bicarbonate (aq., sat., 50 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-30% EtOAc in hexanes, 24-g silica gel column) to afford 1,1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1H-indole-1-carboxylate (1 g, 87% yield) as a (4:1 LCMS, 10:1 by 1H NMR) mixture with the starting material. The mixture was used without further purification. LC-MS (ES) m/z=260, 262 [M+H-t-Bu]+. 1H NMR (400 MHz, DMSO-d6) δ 1.51 (s, 9H), 3.13 (t, J=8.72 Hz, 2H), 3.94-4.08 (m, 2H), 7.26-7.63 (m, 2H).

Provenance & Evidence