N-bromobutanimide → HCID 14770215, 화합물

HRID 2073573노트

반응식

HRID 2073573 반응식
[CH3:1][C:2]1[C:3]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[CH:14][C:6]1[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=1[CH:4]=2.[Br:19]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[C:3]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[CH:14][C:6]1[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=1[CH:4]=2

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 14770214HCID 14770214, 화합물

생성물 1

HCID 14770215HCID 14770215, 화합물수율 101%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

To a RB flask was added 7-methyl-benzo[b]naphtho-[2,3-d]furan (Cambridge Chemicals, Inc., 16.0 g, 0.07 mol), N-bromosuccinimide (Aldrich 12.8 g, 0.072 mol, recrystallized from H2O and dried under high vacuum overnight), a catalytic amount of benzoyl peroxide (0.01 g) and CCl4 (1 L). The mixture was refluxed for 2.5 h, cooled and filtered to remove the succinimide formed in the reaction. The solvent was then removed from the reaction mixture by rotary evaporation. The crude product was purified by flush chromatography on SiO2 using PhCH3 as the eluting solvent. The appropriate fractions were combined and the solvent once again removed by rotary evaporation to give 22.0 g of product. The material (which was one spot by TLC and pure by NMR) was used without further purification.

후처리

  1. temperatureThe mixture was refluxed for 2.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove the succinimide
  5. customformed in the reaction
  6. customThe solvent was then removed from the reaction mixture by rotary evaporation
  7. customThe crude product was purified
  8. customby flush chromatography on SiO2
  9. customthe solvent once again removed by rotary evaporation

출처 및 근거

ORD 기록
ord-6e891e0d153941b9a942bb553f968015
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04918101

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