Phosphorus tribromide → 1,2,3,4,5,6,7,8-octafluoro-9-(pentafluorophenyl)-fluorene

HRID 1793627Notes

Reaction equation

HRID 1793627 reaction equation
[F:1][C:2]1[C:14]2[C:13](O)([C:15]3[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=3[F:25])[C:12]3[C:7](=[C:8]([F:30])[C:9]([F:29])=[C:10]([F:28])[C:11]=3[F:27])[C:6]=2[C:5]([F:31])=[C:4]([F:32])[C:3]=1[F:33].P(Br)(Br)Br>>[F:1][C:2]1[C:14]2[CH:13]([C:15]3[C:16]([F:25])=[C:17]([F:24])[C:18]([F:23])=[C:19]([F:22])[C:20]=3[F:21])[C:12]3[C:7](=[C:8]([F:30])[C:9]([F:29])=[C:10]([F:28])[C:11]=3[F:27])[C:6]=2[C:5]([F:31])=[C:4]([F:32])[C:3]=1[F:33]

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 22022760HCID 22022760, compound

Product 1

HCID 116701081,2,3,4,5,6,7,8-octafluoro-9-(pentafluorophenyl)-fluoreneYield 84%

Procedure

4.5 g (0.009 moles) of 1,2,3,4,5,6,7,8-octafluoro-9-hydroxy-9-(pentafluorophenyl)fluorene thus prepared, are added to 25 ml (0.26 moles) of PBr3 and heated to 1100C for 30 minutes in an inert atmosphere. The reaction mass is hydrolyzed in ice, extracted with ethyl ether, the extract is washed with an aqueous solution (10%) of NaHCO3, dried on sodium sulfate, filtered and dried. The residue is purified by chromatography on a silica gel column (eluant: petroleum ether/methylene chloride, 98/2), obtaining, after evaporation of the pure fractions, 3.61 g of white crystalline product corresponding to the desired product having formula (VI) (yield 84%) (characterization by means of 1H-NMR and

Workup

  1. extractionextracted with ethyl ether
  2. washthe extract is washed with an aqueous solution (10%) of NaHCO3
  3. customdried on sodium sulfate
  4. filtrationfiltered
  5. customdried
  6. customThe residue is purified by chromatography on a silica gel column (eluant: petroleum ether/methylene chloride, 98/2)
  7. customobtaining
  8. customafter evaporation of the pure fractions, 3.61 g of white crystalline product corresponding to the desired product

Sources & evidence

ORD record
ord-74d4123d0b44420aa4af94621d981895
Source dataset
uspto-grants-2006_07
Patent number
US07081505B2

Reaction notes

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