1H-Indene, 2-bromo- → 2-Neopentylindene

HRID 11971

Reaction equation

HRID 11971 reaction equation
Br[C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11]([Mg]Cl)[C:12]([CH3:15])([CH3:14])[CH3:13]>C1COCC1.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>[CH2:11]([C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 5755861H-Indene, 2-bromo-HCID 178418809HCID 178418809, compound

Product 1

HCID 219770112-Neopentylindene

Reagents, catalysts & solvents 2

HCID 178418751HCID 178418751, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-bromoindene (7.5 g, 39 mmol) and 2.5 g of NiCl2(PPh3)2 in 150 mL of THF was added over 1 hour 50 mL of neopentyl magnesium chloride (1.0 M in THF; 50 mmol). The mixture was stirred overnight and then quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (hexanes/silica) as for 2-benzyl-indene. Yield: 4.75 g, 66 percent

Workup

  1. customquenched
  2. additionby adding 150 mL of 1.0 M aqueous hydrochloric acid
  3. customThe product was isolated
  4. custompurified (hexanes/silica) as for 2-benzyl-indene

Sources & evidence

ORD record
ord-d016d5953a644d638a4f6edb144b58b4
Source dataset
uspto-grants-2006_08
Patent number
US07098356B2

Linked notes

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