N-bromobutanimide → HCID 86718010, compound
Reaction equation
[CH3:1][C@@H:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH3:12])[CH:9]=[C:10]([NH2:11])[C:4]=2[O:3]1.C1C(=O)N([Br:20])C(=O)C1>CN(C=O)C>[Br:20][C:7]1[C:5]2[CH2:6][C@@H:2]([CH3:1])[O:3][C:4]=2[C:10]([NH2:11])=[CH:9][C:8]=1[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of (R)-2,5-dimethyl-2,3-dihydrobenzofuran-7-amine (3f) (1.3 g, 7.9 mmol) in DMF (16 mL) was added NBS (1.42 g, 7.9 mmol) at 0° C. It was stirred for 15 min at 0° C. The mixture was extracted with EtOAc (150 mL), washed with NaHSO3 (50 mL), water and 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 (3g) as a solid. MS-ESI (m/z): 242 (M+1)+.
Workup
- extractionThe mixture was extracted with EtOAc (150 mL)
- washwashed with NaHSO3 (50 mL), water and brine
- customdried
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1)
Sources & evidence
- ORD record
- ord-d3f31bc6cd614a608d23b655ff0fbfc2
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206166B2
Reaction notes
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