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Ethanol → 2-Butoxy-1,8-difluoro-7-(4-n-pentylphenyl)fluorene

HRID 1744751
ノート
印刷プレビュー

反応式

HRID 1744751 の反応式
[CH2:1]([O:5][C:6]1[C:18]([F:19])=[C:17]2[C:9]([C:10]3[CH:11]=[CH:12][C:13](B(O)O)=[C:14]([F:20])[C:15]=3[CH2:16]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[CH2:33]([C:38]1[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=1)[CH2:34][CH2:35][CH2:36][CH3:37]>O.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[C:15](=[C:14]([F:20])[C:13]([C:41]4[CH:40]=[CH:39][C:38]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:43][CH:42]=4)=[CH:12][CH:11]=3)[CH2:16][C:17]=2[C:18]=1[F:19])[CH2:2][CH2:3][CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27355991-Bromo-4-pentylbenzeneHCID 222231157-Butoxy-1,8-difluorofluorene-2-boronic acid

生成物 1

HCID 222231232-Butoxy-1,8-difluoro-7-(4-n-pentylphenyl)fluorene

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒2 回
HCID 1140Toluene溶媒

実験手順

12 mmol of 7-butoxy-1,8-difluorofluorene-2-boronic acid (Example 6, 1st stage), 20 ml of ethanol, a solution of 24 mmol of sodium carbonate in 20 ml of water and 1 mol % of tetrakis(triphenylphosphine)palladium(0) are added to a solution of 12 mmol of 4-n-pentylbromobenzene in 40 ml of toluene. The mixture is heated to boiling until the reaction is complete. After cooling, the mixture is admixed with 100 ml of water, the phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with saturated NaCI solution and dried over sodium sulfate, and the solvents are removed under reduced pressure. The crude product is chromatographed on silica gel (2:5 dichloromethane/heptane) and recrystallized from heptane. 2-Butoxy-1,8-difluoro-7-(4-n-pentylphenyl)fluorene is obtained.

後処理

  1. temperatureThe mixture is heated
  2. temperatureAfter cooling
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic phases are washed with saturated NaCI solution
  6. dry with materialdried over sodium sulfate
  7. customthe solvents are removed under reduced pressure
  8. customThe crude product is chromatographed on silica gel (2:5 dichloromethane/heptane)
  9. customrecrystallized from heptane

出典と根拠

ORDレコード
ord-542bfa57cec64f758f5d247622e8e011
出典データセット
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07018685B2

反応ノート

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