4-Chloro-2-(propan-2-yl)-1H-indene → 4-(3,5-Dimethylphenyl)-2-isopropylindene

HRID 844458Notes

Reaction equation

HRID 844458 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]2.[CH3:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[C:19]([CH3:21])[CH:20]=1>CCOCC.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>[CH3:14][C:15]1[CH:16]=[C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]3)[CH:18]=[C:19]([CH3:21])[CH:20]=1

Participants

5

Reactant 2

HCID 219183974-Chloro-2-(propan-2-yl)-1H-indeneHCID 178425074HCID 178425074, compound

Product 1

HCID 220230144-(3,5-Dimethylphenyl)-2-isopropylindene

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

4-chloro-2-isopropylindene (10 g, 54 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Dimethylphenylmagnesium bromide (54 mmol) as a Et20 solution was added under vigorous stirring and the reaction stirred overnight at room temperature. After overnight stirring, the reaction was slowly quenched with H2O to neutralize unreacted Grignard. The solution was subsequently treated with 100 mL of 10% HCl(aq), and neutralized with saturated sodium bicarbonate aqueous solution. The 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.

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. stirringAfter overnight stirring
  3. customthe reaction was slowly quenched with H2O
  4. additionThe solution was subsequently treated with 100 mL of 10% HCl(aq)
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. customthe solvent was removed by rotary evaporation
  7. washeluted with hexane

Sources & evidence

ORD record
ord-922256e549bd48079101684d50f42aca
Source dataset
uspto-grants-2002_04
Patent number
US06380334B1

Reaction notes

Loading…