Triethylamine → HCID 21568316, compound

HRID 1579309Notes

Reaction equation

HRID 1579309 reaction equation
BrN1C(=O)CCC1=O.Br[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[P:12](=[O:21])([CH:19]=[CH2:20])[CH:11]=1.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl.[Hg]>[CH:19]([P:12]1(=[O:21])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)=[CH2:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 21568333HCID 21568333, compound

Product 1

HCID 21568316HCID 21568316, compound

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-vinylphosphindoline 1-oxide (6.4g, 36.0 mmol) in carbon tetrachloride (80 ml) was added N-bromosuccinimide (6.8g, 38.6 mmol) and the two phase mixture stirred under reflux whilst being irradiated with a 500 watt mercury lamp. After 15 mins the solution was washed with water, the washings were extracted with chloroform and the combined organic extract was dried and evaporated to give a light yellow oil. A p.m.r. spectrum of this indicated that it was 3-bromo-1-vinylphosphindole 1-oxide. This material was heated under reflux with triethylamine (10 ml) for 5 mins, cooled, and the precipitated hydrobromide filtered off. The benzene filtrate was washed with water, dried and evaporated. Distillation gave an oil (5.8g, b.p. 170°/0.01 min), g.l.c. of which showed it to be about 90% pure.

Workup

  1. temperatureunder reflux
  2. washAfter 15 mins the solution was washed with water
  3. extractionthe washings were extracted with chloroform
  4. extractionthe combined organic extract
  5. customwas dried
  6. customevaporated
  7. customto give a light yellow oil
  8. temperatureThis material was heated
  9. temperaturecooled
  10. filtrationthe precipitated hydrobromide filtered off
  11. washThe benzene filtrate was washed with water
  12. customdried
  13. customevaporated
  14. distillationDistillation
  15. customgave an oil (5.8g, b.p. 170°/0.01 min)

Sources & evidence

ORD record
ord-42199ea5533845b597a9d8e9a8c3420f
Source dataset
uspto-grants-1976_01
Patent number
US03931196

Reaction notes

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