1-Bromooctane → 2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

HRID 1172020노트

반응식

HRID 1172020 반응식
[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4=[C:13]2[C:4](=[CH:5][CH:6]=[C:7]4[CH:8]=[C:9]([Br:17])[CH:10]=3)[CH:3]=1.C(Br)CCCCCCC.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[C:9]([Br:17])[CH:10]=3)[CH:3]=1

참가 물질

7

반응물 3

HCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 594310762,6-dibromo-4H-cyclopenta[def]phenanthrene

생성물 1

HCID 125243672,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene수율 133.6%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

2,6-dibromo-4H-cyclopenta[def]phenanthrene (2.6 g, 7.7 mmol) and octyl bromide (3.6 g, 18.5 mmol) in a 50 ml round bottom flask were dissolved with toluene (10 ml), and tetrabutylammoniumbromide (TBAB) (0.125 g, 0.385 mmol) was added thereto. A solution of NaOH (3.1 g, 77 mmol) in water (50 ml) was added to the reaction mixture, and the resultant solution was refluxed for two days. After the reaction was terminated, the reaction solution was extracted with chloroform. The organic phase was dried over MgSO4, concentrated, and purified by silica gel column chromatography (eluent: n-hexane). The eluate was distilled under a reduced pressure to remove unreacted octyl bromide, thereby giving a compound 2 (3.6 g, 80%).

후처리

  1. additionwas added
  2. customAfter the reaction was terminated
  3. extractionthe reaction solution was extracted with chloroform
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (eluent: n-hexane)
  7. distillationThe eluate was distilled under a reduced pressure
  8. customto remove unreacted octyl bromide

출처 및 근거

ORD 기록
ord-acf87e69a6a146ed983bba7ce1f9e29f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07833635B2

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