4-Chloro-2-(propan-2-yl)-1H-indene → HCID 18386460, compound

HRID 993309Notes

Reaction equation

HRID 993309 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:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Mg]Br>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:20]=[CH:19][CH:18]=[CH:17][C:16]=1[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

Participants

5

Reactant 2

HCID 219183974-Chloro-2-(propan-2-yl)-1H-indeneHCID 178424303HCID 178424303, compound

Product 1

HCID 18386460HCID 18386460, compound

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

4-Chloro-2-isopropylindene (9.8 g, 51 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) are dissolved in 150 mL of Et2O. 2-Methylphenylmagnesium bromide (51 mmol) as an 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) 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. Yield was 6.6 g (52%).

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-6cf1f972c2644d3aa5a622c8525a6263
Source dataset
uspto-grants-2002_10
Patent number
US06472474B2

Reaction notes

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