Water → 1-Fluoro-7-propyl-2-(3,4,5-trifluorophenyl)phenanthrene

HRID 1830483Notes

Reaction equation

HRID 1830483 reaction equation
[F:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)=[CH:4][CH:5]=[C:6]2[C:15]=1[CH2:14][CH2:13][C:12]1[CH:11]=[C:10]([CH2:16][CH2:17][CH3:18])[CH:9]=[CH:8][C:7]2=1.BrN1C(=O)CCC1=O.O>C1C=CC=CC=1>[F:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=2)=[CH:4][CH:5]=[C:6]2[C:15]=1[CH:14]=[CH:13][C:12]1[CH:11]=[C:10]([CH2:16][CH2:17][CH3:18])[CH:9]=[CH:8][C:7]2=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22045686HCID 22045686, compound

Product 1

HCID 220447941-Fluoro-7-propyl-2-(3,4,5-trifluorophenyl)phenanthrene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

8-fluoro-2-propyl-7-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene produced in Example 1 was dissolved in benzene, NBS (N-bromosuccinimide) and AIBN (2,2-azobis isobutyronitrile) were added, and the temperature was gradually raised to benzene reflux temperature. Stirring was then continued for a further 2 hours, before water was added and the reaction halted, and the organic layer was then separated. The aqueous layer was extracted with toluene and this extract was combined with the organic layer, which was then washed with water and a saturated aqueous solution of sodium chloride, before being dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the whole crude product was dissolved in ethyl acetate, and 5% palladium/carbon (wet) was then added, and the mixture was stirred in an autoclave under a hydrogen pressure of 4 Kg/cm2. After 5 hours stirring at room temperature, the catalyst was removed by filtration through celite, and the solvent was then removed by evaporation. The crude product was purified by silica gel column chromatography (hexane) and then recrystallized 3 times from ethanol to yield 8-fluoro-2-propyl-7-(3,4,5-trifluorophenyl)phenanthrene.

Workup

  1. temperaturereflux temperature
  2. additionwas added
  3. customthe organic layer was then separated
  4. extractionThe aqueous layer was extracted with toluene
  5. washwas then washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, before being dried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation
  8. dissolutionthe whole crude product was dissolved in ethyl acetate
  9. addition5% palladium/carbon (wet) was then added
  10. stirringthe mixture was stirred in an autoclave under a hydrogen pressure of 4 Kg/cm2
  11. stirringAfter 5 hours stirring at room temperature
  12. customthe catalyst was removed by filtration through celite
  13. customthe solvent was then removed by evaporation
  14. customThe crude product was purified by silica gel column chromatography (hexane)
  15. customrecrystallized 3 times from ethanol

Sources & evidence

ORD record
ord-68686cd133924fbd806e7afda6362303
Source dataset
uspto-grants-2006_06
Patent number
US07067179B1

Reaction notes

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