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

HRID 742820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 742820
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 152942577-Bromo-5-chloro-2,3-dihydro-1-benzofuran-4-amineAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dcfc9f7b622f4e3e9cf2df8091a88e8a
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05554772

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