Potassium Carbonate → 6-Bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine

A mixture of the product 5-bromo-2-(2-bromoethoxy)benzenamine (250 mg, 0.848 mmol) and K2CO3 (234 mg, 1.695 mmol) in DMF (5 mL) was stirred at 60° C. for 4 h. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (3×50 mL) and brine (50 mL), concentrated to give 6-bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine (170 mg, 94%) as a yellow oil. LCMS: 214 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 3.26 (m, 2H), 4.08 (t, J=4.8 Hz, 2H), 6.06 (s, 1H), 6.56 (m, 2H), 6.69 (d, J=1.6 Hz, 1H).

1. extractionextracted with ethyl acetate (100 mL)
2. washThe organic layer was washed with water (3×50 mL) and brine (50 mL)
3. concentrationconcentrated

ORD record

ord-5462fb0c29b14cab949986a1b5b8197e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906909B2