4-Bromo-2,5-dimethyl-1h-indene → 2,5-Dimethyl-4-phenylindene

HRID 1372538Notes

Reaction equation

HRID 1372538 reaction equation
Br[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:12])[CH2:6]2.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:5]1[CH2:6][C:7]2[C:3]([CH:4]=1)=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([CH3:11])=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 231154544-Bromo-2,5-dimethyl-1h-indeneHCID 178418255HCID 178418255, compound

Product 1

HCID 231154562,5-Dimethyl-4-phenylindene

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

4-Bromo-2,5-dimethylindene (9.0 g, 40 mmol), prepared as described under I.(b) above, and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 300 ml of diethyl ether (Et2O). Phenylmagnesium bromide, 3.0 M in Et2O, (13.5 ml, 40 mmol) was added under vigorous stirring and the reaction stirred overnight at reflux. The resultant reaction was slowly quenched with H2O to neutralize unreacted Grignard reagent, subsequently treated with 100 ml of 10% HCl(aq), and neutralized with saturated sodium bicarbonate aqueous solution. The resultant organic layer was dried with magnesium sulfate, and the solvent was removed by rotary evaporation. The remaining residue was loaded onto a silica gel column and eluted with hexane. Yield is 1.3 g (15%).

Workup

  1. stirringthe reaction stirred overnight
  2. temperatureat reflux
  3. customThe resultant reaction
  4. customwas slowly quenched with H2O
  5. additionsubsequently treated with 100 ml of 10% HCl(aq)
  6. dry with materialThe resultant organic layer was dried with magnesium sulfate
  7. customthe solvent was removed by rotary evaporation
  8. washeluted with hexane

Sources & evidence

ORD record
ord-521cbc1d20c3480697c10f38a8226be0
Source dataset
uspto-grants-2007_01
Patent number
US07157591B2

Reaction notes

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