Potassium Carbonate → 6-Bromo-3,4-dihydro-2H-benzo[b][1,4]oxazine
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH2:11]Br)=[C:6]([NH2:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:10][CH2:11][NH:8][C:6]=2[CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
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).
Workup
- extractionextracted with ethyl acetate (100 mL)
- washThe organic layer was washed with water (3×50 mL) and brine (50 mL)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-20d1c575855a4928805ab450fdf58eba
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367663B2
Reaction notes
Loading…