1H-Indene, 2-bromo- → 2-Benzyl-1H-indene

HRID 11964

Reaction equation

HRID 11964 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]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(OCC)C>[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]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 5755861H-Indene, 2-bromo-HCID 178418336HCID 178418336, compound

Product 1

HCID 128582792-Benzyl-1H-indene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A 500 mL 3 neck flask was charged with 2.5 g (13 mmol) of 2-bromo-indene, 50 mg of NiCl2(1,3-bis(diphenylphosphino)propane) (0.06 mmol) and 150 mL of diethyl ether. To this mixture was added dropwise 12.8 mL of 1.0 M benzyl magnesium chloride in ether (12.8 mmol). The reaction was heated to reflux overnight and then quenched by cooling to 0° C. and adding 150 mL of 1.0 M aqueous hydrochloric acid. The organic layer was separated and washed twice with 50 mL of ether. The organic extracts were combined, dried over magnesium sulfate, filtered and the volatiles removed in vacuo to leave a dark oil. The sample was dissolved in a small amount of hexanes and purified by flash column chromatography using silica and hexanes as the elutent. Yield: 1.75 g, 66 percent

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. customquenched
  4. additionadding 150 mL of 1.0 M aqueous hydrochloric acid
  5. customThe organic layer was separated
  6. washwashed twice with 50 mL of ether
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe volatiles removed in vacuo
  10. customto leave a dark oil
  11. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-b447cd02024a491a92ae1236be790cec
Source dataset
uspto-grants-2006_08
Patent number
US07098356B2

Linked notes

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