N-bromobutanimide → HCID 86718002, compound
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[Br:19][C:10]1[C:6]2[CH2:7][CH2:8][O:9][C:5]=2[C:4]([NH2:11])=[CH:3][C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 5-methyl-2,3-dihydrobenzofuran-7-amine (1d) (1.0 g, 6.7 mmol) in DMF (21 mL) at 0° C., was added NBS (1.19 g, 6.7 mmol), it was stirred at 0° C., for 15 min. The mixture was extracted with EtOAc (150 mL), washed with saturated NaHSO3 (50 mL), water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1) to give the title compound (1e) as a yellow solid. MS-ESI (m/z): 228 (M+1)+.
Workup
- extractionThe mixture was extracted with EtOAc (150 mL)
- washwashed with saturated NaHSO3 (50 mL), water, brine
- customdried
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1)
Sources & evidence
- ORD record
- ord-a29238825bde4c5998fa3ff4d3ceb847
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206166B2
Reaction notes
Loading…