Toluene → 2-Bromo-9,9-diethylfluorene

HRID 720015

反応式

HRID 720015 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 121238752-Bromo-9,9-diethylfluorene収率 82%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-ba321da493ae41c39fd83ed158c1ffdf
出典データセット
uspto-grants-2006_11
特許番号
US07132572B2

関連ノート

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