N-bromobutanimide → 5,6-Dibromo-2,3-dihydrobenzofuran

HRID 2272213Notes

Reaction equation

HRID 2272213 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]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 112526166-Bromo-2,3-dihydro-1-benzofuran

Product 1

HCID 584868825,6-Dibromo-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. extractionextracted with EA
  2. washphase was washed with aq. sodium bicarbonate and brine subsequently
  3. dry with materialAfter dried over sodium sulfate the org
  4. concentrationphase was concentrated

Sources & evidence

ORD record
ord-f10f7ef7964346909c55bc8058adda4f
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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