N-bromobutanimide → 5,6-Dibromo-2,3-dihydrobenzofuran
Reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][CH2:16][O:15][C:14]=2[CH:18]=1>C(#N)C>[Br:8][C:11]1[C:10]([Br:9])=[CH:18][C:14]2[O:15][CH2:16][CH2:17][C:13]=2[CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
NBS (450 mg, 2.53 mmol) was added to a solution of 6-bromo-2,3-dihydrobenzo[b]furan (137) (504 mg, 2.53 mmol) in 15 ml ACN. The reaction mixture was stirred overnight at r.t. The yellow solution was poured into ice-water, extracted with EA. Org. phase was washed with aq. sodium bicarbonate and brine subsequently. After dried over sodium sulfate the org. phase was concentrated to give 676 mg (purity ca. 90%) title compound as dark oil which solidified after standing at r.t.
Workup
- extractionextracted with EA
- washphase was washed with aq. sodium bicarbonate and brine subsequently
- dry with materialAfter dried over sodium sulfate the org
- concentrationphase was concentrated
Sources & evidence
- ORD record
- ord-f10f7ef7964346909c55bc8058adda4f
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120751B2
Reaction notes
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