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

HRID 742104노트

반응식

HRID 742104 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-984b32021a5249ac909448c2942ef1f0
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552553

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