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

HRID 1744751
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HRID 1744751 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매2회
HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-542bfa57cec64f758f5d247622e8e011
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07018685B2

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