N-bromobutanimide → 7-Bromo-5-chloro-2,3-dihydro-1-benzofuran-4-amine

HRID 52668Notes

Reaction equation

HRID 52668 reaction equation
[Cl:1][C:2]1[C:10]([NH2:11])=[C:6]2[CH2:7][CH2:8][O:9][C:5]2=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:12][C:4]1[CH:3]=[C:2]([Cl:1])[C:10]([NH2:11])=[C:6]2[C:5]=1[O:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 126697005-Chloro-2,3-dihydro-1-benzofuran-4-amine

Product 1

HCID 152942577-Bromo-5-chloro-2,3-dihydro-1-benzofuran-4-amineYield 87.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 9.1 parts of 5-chloro-2,3-dihydro-4-benzofuranamine [described in J. Het. Chem., 17(6) 1333 (1980)], 9.6 parts of N-bromosuccinimide and 130.5 parts of benzene was stirred for 1 hour at reflux temperature. The solvent was evaporated and the residue was dissolved in 387.4 parts of trichloromethane. The solution was washed with water (2×200 parts). The organic layer was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; C6H14 /CH2Cl2 50:50). The eluent of the desired fraction was evaporated, yielding 11.8 parts (87.9%) of 7-bromo-5-chloro-2,3-dihydro-4-benzofuranamine (interm. 8).

Workup

  1. temperatureat reflux temperature
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 387.4 parts of trichloromethane
  4. washThe solution was washed with water (2×200 parts)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; C6H14 /CH2Cl2 50:50)
  9. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-d40256ca342e44c19228c08cd2002cfd
Source dataset
uspto-grants-1997_04
Patent number
US05616738

Reaction notes

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