N-bromobutanimide → 5-Bromo-2,3-dihydro-1-benzofuran

HRID 2247416Notes

Reaction equation

HRID 2247416 reaction equation
COC(/C=C/[C:7]1[CH:12]=[C:11](O)[C:10]2[O:14][CH:15](C3C=CC(O)=C(O)C=3)[CH:16](C(OC)=O)[C:9]=2[CH:8]=1)=O.[Br:29]N1C(=O)CCC1=O>C(#N)C>[Br:29][C:7]1[CH:12]=[CH:11][C:10]2[O:14][CH2:15][CH2:16][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 5857314Dihydrobezofuran

Product 1

HCID 27761595-Bromo-2,3-dihydro-1-benzofuranYield 331.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dihydrobenzofuran (9.34 g) was dissolved in 130 ml of acetonitrile, 13.9 g of N-bromosuccinimide was added thereto and the mixture was stirred at room temperature for 3 hours. The solvent was evaporated, then the residue was dissolved in ethyl acetate and successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed, to give 15.94 g of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washsuccessively washed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-549d7ac1e7cd483fa564e3b97750a56c
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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