Ammonium Chloride → HCID 22227113, compound

HRID 1745870Notes

Reaction equation

HRID 1745870 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][CH:8]=[CH:7]2.[CH:11]([Mg]Br)([CH3:13])[CH3:12].[Cl-].[NH4+]>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ni]Cl>[CH:11]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][CH:8]=[CH:7]2)([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 133302097-Bromo-1H-indeneHCID 178418365HCID 178418365, compound

Product 1

HCID 22227113HCID 22227113, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 2734542[1,2-Bis(diphenylphosphino)ethane]dichloronickel(II)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Using a 300 ml three-necked flask as the reactor, under a nitrogen stream, 1.36 g (2.57 millimoles) of [1,2-bis(diphenylphosphino)ethane]dichloronickel(II) was dissolved in 20 ml of tetrahydrofuran. To this suspension there was added a solution of 10 g (51.30 millimoles) of 7-bromoindene in 100 ml of tetrahydrofuran, prepared based on the method described in J. Org. Chem. 49, 4226–4237(1984). After dropwise addition of 51 ml (102.60 millimoles) of isopropylmagnesium bromide (2N) to the mixed solution while cooling on ice, the mixture was heated to reflux for 20 hours. After reflux, hydrolysis was performed with a saturated aqueous solution of ammonium chloride, distilled water was added, extraction was performed several times with diethyl ether, and then the extract was washed once with saturated saline and dried over anhydrous magnesium sulfate. After drying, the magnesium sulfate was filtered off and the solvent was purified with a silica gel column to obtain 7.14 g of 7-isopropylindene as a yellow oil (88% yield).

Workup

  1. customprepared
  2. temperaturewhile cooling on ice
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 20 hours
  5. temperatureAfter reflux
  6. customhydrolysis
  7. distillationdistilled water
  8. additionwas added
  9. extractionextraction
  10. washthe extract was washed once with saturated saline
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customAfter drying
  13. filtrationthe magnesium sulfate was filtered off
  14. customthe solvent was purified with a silica gel column

Sources & evidence

ORD record
ord-e27ff52da0e140a592000e3342df5acc
Source dataset
uspto-grants-2006_03
Patent number
US07019157B2

Reaction notes

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