Toluene → 2-Bromo-9,9-diethylfluorene

HRID 720015

반응식

HRID 720015 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-].[Na+].I[CH2:18][CH3:19].[C:20]1(C)C=CC=C[CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:18][CH3:19])([CH2:20][CH3:21])[C:4]=2[CH:3]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 6340IodoethaneHCID 143362-Bromo-9H-fluoreneHCID 14798Sodium Hydroxide

생성물 1

HCID 121238752-Bromo-9,9-diethylfluorene수율 82%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-bromofluorene (2.5 g, 10 mmol) in toluene (40 ml) was added tetrabutylammonium bromide (0.8 g, 2.48 mmol) as a phase transfer catalyst. A freshly prepared solution of aqueous sodium hydroxide (25 ml, 50% w/w) was added at once to the solution. The mixture turned orange and became viscous. To this solution, iodoethane (2.4 ml, 30 mmol) was added. The mixture was stirred at 60° C. for a period of 8 h. It was diluted with ethyl acetate (25 ml) and washed several portions of water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product liquid. The products were purified by column chromatography (silica gel, hexane as eluent, Rf=0.8 on thin layer chromatography) giving colorless oil of 2-bromo-9,9-diethylfluorene (2.5 g) in a yield of 82%.

후처리

  1. washwashed several portions of water
  2. dry with materialOrganic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuuo
  4. customto afford the crude product liquid
  5. customThe products were purified by column chromatography (silica gel, hexane as eluent, Rf=0.8 on thin layer chromatography)

출처 및 근거

ORD 기록
ord-ba321da493ae41c39fd83ed158c1ffdf
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132572B2

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