HCID 22471914, compound → HCID 22117972, compound

HRID 844466Notes

Reaction equation

HRID 844466 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[CH2:6]2.[F:12][C:13]([F:27])([F:26])[C:14]1[CH:15]=[C:16]([Mg]Br)[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=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>[F:12][C:13]([F:26])([F:27])[C:14]1[CH:15]=[C:16]([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:17]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:19]=1

Participants

5

Reactant 2

HCID 22471914HCID 22471914, compoundHCID 178506227HCID 178506227, compound

Product 1

HCID 22117972HCID 22117972, compound

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

4-Bromo-2-methylindene (10.7 g, 51 mmol) and NiCl2(PPh3)2(1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-bis(trifluoromethyl)phenylmagnesium bromide (51 mmol) as a Et2O 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. Yield was 2.2 g (13%).

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-76a074ebdc9a4dc196cbbbd9935f4927
Source dataset
uspto-grants-2002_04
Patent number
US06380330B1

Reaction notes

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