Carbon tetrabromide → Triphenylphosphine Oxide

HRID 2398096Notes

Reaction equation

HRID 2398096 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Br)(Br)(Br)Br.[N+](C1OC(C=O)=CC=1)([O-])=[O:26]>C(Cl)Cl.[Zn]>[C:14]1([P:7](=[O:26])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 127745-Nitrofurfural

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 6.5 g of zinc dust in 300 ml of methylene chloride was added, successively, 26.2 g of triphenylphosphine and 33.2 g of carbon tetrabromide. A mildly exothermic reaction carried the temperature of the mixture to 35°-40°, no cooling being applied. The mixture then was stirred for one hour at room temperature, then cooled to 15° and treated with 10.7 g of 5-nitro-2-furaldehyde. The mixture then was stirred overnight at 25° and filtered to remove suspended salt. The filtrate was concentrated under reduced pressure and the residue was extracted with two 200 ml portions of ether. The combined ether extracts were concentrated to a volume of about 100 ml, diluted with an equal volume of pentane, and cooled. Filtration gave triphenylphosphine oxide. The filtrate was concentrated under reduced pressure and the residue was recrystallized from either/pentane (1:2) to give a solid, m.p.: 73°-78°. Recrystallization of the solid from either/pentane (1:4) gave 2 as yellow prisms, m.p.: 76°-78°.

Workup

  1. additionwas added
  2. customA mildly exothermic reaction
  3. customto 35°-40°
  4. temperaturecooled to 15°
  5. stirringThe mixture then was stirred overnight at 25°
  6. filtrationfiltered
  7. customto remove
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. extractionthe residue was extracted with two 200 ml portions of ether
  10. concentrationThe combined ether extracts were concentrated to a volume of about 100 ml
  11. additiondiluted with an equal volume of pentane
  12. temperaturecooled
  13. filtrationFiltration

Sources & evidence

ORD record
ord-ea0e52a5e7b548aabc19b2fb9b8056de
Source dataset
uspto-grants-1977_05
Patent number
US04024161

Reaction notes

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