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

HRID 1036116Notes

Reaction equation

HRID 1036116 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-6261de30ab2b4d1286b75c9d56757b55
Source dataset
uspto-grants-2013_10
Patent number
US08546403B2

Reaction notes

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