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

HRID 1744751Notes

Reaction equation

HRID 1744751 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-542bfa57cec64f758f5d247622e8e011
Source dataset
uspto-grants-2006_03
Patent number
US07018685B2

Reaction notes

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