N-bromobutanimide → HCID 21460235, compound

Participants

Reaction Steps

2-(4-morpholinyl)-4H-benzopyran-4-one (2.0 g, 8.0 mmol) is dissolved in CH2Cl2 (20 mL). N-Bromosuccinimide (1.6 g, 8.2 mmol) is added and the reaction mixture waned slightly and the starting material disappears immediately as evidenced by TLC. The solvent is removed in vacuo and the colorless residue is taken up in EtOAc (200 mL) and washed with water (4×30 mL), brine (50 mL) and dried (MgSO4). Rotary evaporation gives the desired product (2.27 g, 92%) as colorless crystals. mp: 145°-6° c ; IR (mull) 3337, 3016, 2922, 2871, 2855, 1698, 1609, 1585, 1502, 1462, 1378, 1367, 1341, 1303, 1295, 1260, 1234, 996, 812 cm-1 ; 1H NMR (CDCl3, δ) 8.22 (dd, J=7.9, 1.8 Hz, 1H), 7.63 (ddd, J=8.2, 7.4, 1.4 Hz, 1H), 7.44-7.28 (m, 2H), 3.90-3.84 (m, 4H), 3.76-3.69 (m, 4H); LRMS m/e (rel intensity) 311 (55), 309 (55), 253 (14), 231 (17), 230 (100), 172 (21), 121 (20), 120 (15), 110 (61), 41 (16); UV (EtOH) λ max (ε) 216 (18,400), 238 (18,600), 317 (17,040); High resolution MS calc'd. for C13H12 NO3Br: 309.0001. Found: 308.9990. Anal. calc'd. for C13 H12NO3Br: C, 50.34; H, 3.90; N,4.52. Found: C, 50.40; H,4.05; N, 4.46.

Provenance & Evidence