4-Chloro-2-methyl-1H-indene → 4-(3',5'-Dimethylphenyl)2-methylindene

HRID 2417353Notes

Reaction equation

HRID 2417353 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[CH2:6]2.[CH3:12][C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[C:17]([CH3:19])[CH:18]=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>[CH3:12][C:13]1[CH:14]=[C:15]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH3:11])[CH2:6]3)[CH:16]=[C:17]([CH3:19])[CH:18]=1

Participants

5

Reactant 2

HCID 120107424-Chloro-2-methyl-1H-indeneHCID 178425074HCID 178425074, compound

Product 1

HCID 179395644-(3',5'-Dimethylphenyl)2-methylindene

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

4-Chloro-2-methylindene (8.9 g, 54 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Dimethylphenylmagnesium bromide (10 g, 54 mmol) as a Et2O solution was added to the solution and the reaction was 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), 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. Yield was 5.6 g (44%).

Workup

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

Sources & evidence

ORD record
ord-2679e546b47b43229d1f2b1713c4f264
Source dataset
uspto-grants-2004_11
Patent number
US06825372B2

Reaction notes

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