N-bromobutanimide → HCID 118074739, compound

HRID 1775442Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Br:18]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C>[Br:18][C:7]1[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:9][C:4]2[CH2:3][CH2:2][O:1][C:5]=2[CH:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of tert-butyl (2,3-dihydro-1-benzofuran-5-yl)carbamate (410 mg) and acetonitrile (9.00 mL) was added N-bromosuccinimide (341 mg), followed by stirring at 65° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 92:8) to obtain tert-butyl (6-bromo-2,3-dihydro-1-benzofuran-5-yl)carbamate (178 mg) as a colorless solid.

Workup

temperatureAfter cooling to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe insoluble materials were separated by filtration
concentrationthe filtrate was concentrated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 92:8)

Sources & evidence

ORD record: ord-56fedb20397d4cb1a7cbc6f33521e350
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260445B2

Reaction notes

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