Bromine → 4,8-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Temperature

0 °C

To a solution of 8-bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one (1.2 g, 5 mmol) in diethyl ether (20 mL) at 0° C. was added bromine (257 μL, 5 mmol) dropwise under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, allowed to warm up to RT and stirred for 3 h. Further bromine (50 μL, 0.97 mmol) was added and stirring was pursued for 16 h. The solvent was removed in vacuo and the resultant residue was purified by flash chromatography (SiO2, 10% ethyl acetate in cyclohexane) to give the title compound as a white solid (1.55 g, 97%). 1H NMR (CDCl3): 7.62 (1 H, m), 7.26 (2 H, m), 4.94 (1 H, dd, J=7.7, 6.7 Hz), 4.43 (1 H, ddd, J=12.7, 5.6, 4.8 Hz), 4.25-4.15 (1 H, m), 2.97-2.86 (1 H, m), 2.51 (1 H, ddt, J=14.7, 7.7, 4.6 Hz).

1. temperatureto warm up to RT
2. stirringstirred for 3 h
3. stirringstirring
4. waitwas pursued for 16 h
5. customThe solvent was removed in vacuo
6. customthe resultant residue was purified by flash chromatography (SiO2, 10% ethyl acetate in cyclohexane)

ORD record

ord-8745b201fb704f02a64425378ece9978

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399690B2