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

HRID 1358731Notes

Reaction equation

HRID 1358731 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 84.2%

Conditions

Temperature
110 °C

Procedure

4.5 g (0.009 moles) of 1,2,3,4,5,6,7,8-octafluoro-9-hydroxy-9-(pentafluorophenyl)fluorene (XII), prepared as described in the preceeding example 7, are added to 25 ml (0.26 moles) of PBr3 and heated to 110° C. 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 (yield 84%).

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

Sources & evidence

ORD record
ord-53ae9c9f5fec4551a337be9950b098a9
Source dataset
uspto-grants-2003_07
Patent number
US06596891B1

Reaction notes

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