Triethyl Phosphate → HCID 13836140, compound

HRID 1886203Notes

Reaction equation

HRID 1886203 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH3:9].[P:10](OCC)([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:11]>[Ni](Cl)Cl.O>[CH2:13]([O:12][P:10]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH3:9])([O:15][CH2:16][CH3:17])=[O:11])[CH3:14]

Participants

5

Reactant 2

HCID 6535Triethyl PhosphateHCID 684723-Bromo-o-xylene

Product 1

HCID 13836140HCID 13836140, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 962WaterSolvent

Procedure

A mixture solution of 25.0 g (0.135 mol) of 3-bromo-o-xylene and 2.0 g (0.015 mol) of anhydrous nickel chloride was heated to 150° to 160° C., to which 26.9 g (0.162 mol) of triethyl phosphate was added for 1 to 2 hours. After the completion of the addition, it was mixed at that temperature and then cooled. To the cooled solution, 30 ml of water was added and mixed for another 30 minutes. It was then extracted three time with 100 ml of diethyl ether. The extracted solution was rinsed three times with a 5% sodium hydrogencarbonate solution and dried with anhydrous sodium sulfate. The ether solution was condensed and subjected to column chromatography to obtain 20 g of transparent liquid which had a chart (FIG. 2) of NMR spectrum in CDCl3 to find the following chemical structure; ##STR14##

Workup

  1. additionwas added for 1 to 2 hours
  2. additionAfter the completion of the addition, it
  3. additionwas mixed at that temperature
  4. temperaturecooled
  5. additionmixed for another 30 minutes
  6. extractionIt was then extracted three time with 100 ml of diethyl ether
  7. washThe extracted solution was rinsed three times with a 5% sodium hydrogencarbonate solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. customcondensed

Sources & evidence

ORD record
ord-20bc59aa63d441c7a8e17dbcc948b6b2
Source dataset
uspto-grants-1992_09
Patent number
US05149847

Reaction notes

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