N-bromobutanimide → HCID 67451842, compound

Participants

Reaction Steps

To a solution of 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (5.21 g, 17.61 mmol) in DCM (176 ml) was added NBS (3.45 g, 19.38 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica 330 g, 5 to 30% EtOAc in hexane), to give 4-bromo-5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (6.16 g). MS: M+H=376. H1NMR (400 MHz, CDCl3) δ: 7.28 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 4.01 (dt, J=11.7 Hz, 3.6 Hz, 2H), 3.50 (td, J=11.7 Hz, 2.7 Hz, 2H), 3.09-2.98 (m, 1H), 2.02-1.86 (m, 4H).

Provenance & Evidence