Phosphorus tribromide → HCID 22022774, compound

HRID 1358730Notes

Reaction equation

HRID 1358730 reaction equation
[F:1][C:2]1[C:14]2[C:13](O)([C:15]3[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=3)[C:12]3[C:7](=[C:8]([F:33])[C:9]([F:32])=[C:10]([F:31])[C:11]=3[F:30])[C:6]=2[C:5]([F:34])=[C:4]([F:35])[C:3]=1[F:36].P(Br)(Br)Br>>[F:1][C:2]1[C:14]2[CH:13]([C:15]3[CH:20]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:18]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:16]=3)[C:12]3[C:7](=[C:8]([F:33])[C:9]([F:32])=[C:10]([F:31])[C:11]=3[F:30])[C:6]=2[C:5]([F:34])=[C:4]([F:35])[C:3]=1[F:36]

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 18185768HCID 18185768, compound

Product 1

HCID 22022774HCID 22022774, compoundYield 76.6%

Procedure

g (0.002 moles) of the product (X), obtained according to the preparation reported in the preceeding example 5, are heated with 10 ml (0.105 moles) of PBr3 to 110° C. for 40 minutes. The reaction mass is hydrolyzed in ice, extracted with ethyl ether, the ether extract is washed with an aqueous solution of NaHCO3 (10%), dried on Na2SO4, filtered and the ether solution is dried. The residue is dissolved in 20 ml of acetic acid and 1 g of Zn in powder form is added. The mixture is stirred for 1 h at room temperature, hydrolyzed in water and then extracted with ethyl ether. The ether extract is neutralized with an aqueous solution of NaHCO3 (10%), dried with Na2SO4, filtered and dried. The residue is purified on a silica gel column (eluant petroleum ether) obtaining, after evaporation of the pure fractions, 0.8 g of pure product (yield 76.6%).

Workup

  1. extractionextracted with ethyl ether
  2. extractionthe ether extract
  3. washis washed with an aqueous solution of NaHCO3 (10%)
  4. customdried on Na2SO4
  5. filtrationfiltered
  6. dry with materialthe ether solution is dried
  7. dissolutionThe residue is dissolved in 20 ml of acetic acid
  8. addition1 g of Zn in powder form is added
  9. extractionextracted with ethyl ether
  10. extractionThe ether extract
  11. dry with materialdried with Na2SO4
  12. filtrationfiltered
  13. customdried
  14. customThe residue is purified on a silica gel column (eluant petroleum ether)
  15. customobtaining

Sources & evidence

ORD record
ord-c5e5993ae24646a8ad68c2ba16879677
Source dataset
uspto-grants-2003_07
Patent number
US06596891B1

Reaction notes

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