Magnesium Bromide → 2-(3,5-di-t-Butylphenyl)indene

HRID 1061486Notes

Reaction equation

HRID 1061486 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:3]=1.C([Li])(C)(C)C.[Br-].[Mg+2].[Br-].Br[C:25]1[CH2:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2>CCOCC>[C:12]([C:4]1[CH:3]=[C:2]([C:25]2[CH2:33][C:32]3[C:27]([CH:26]=2)=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 82241Magnesium BromideHCID 5755861H-Indene, 2-bromo-HCID 6201361-Bromo-3,5-di-tert-butylbenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 222838282-(3,5-di-t-Butylphenyl)indeneYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Bromo-3,5-di-t-butylbenzene (47.2 g, 0.175 mol) was dissolved in ether (500 mL) and cooled to −70° C. t-Butyllithium (200 mL of 1.7 M solution in pentane, 0.34 mol) was added at −70° C. over a two hour period. The solution was allowed to warm to room temperature slowly. Magnesium bromide etherate (46.5 g, 0.18 mol) was added and the slurry was stirred for one hour. The mixture was then cooled to 5° C. and 2-bromoindene (34.2 g, 0.18 mol) was added. The mixture was warmed to room temperature and then refluxed for three hours. The solution was cooled to room temperature and the reaction was quenched carefully with water. The layers were separated and the organics washed with salt brine and dried over magnesium sulfate. The solvents were evaporated and the product was distilled twice and recrystallized from hexane to give 37.1 g of product (70%).

Workup

  1. additionwas added at −70° C. over a two hour period
  2. temperatureThe mixture was then cooled to 5° C.
  3. temperatureThe mixture was warmed to room temperature
  4. temperaturerefluxed for three hours
  5. temperatureThe solution was cooled to room temperature
  6. customthe reaction was quenched carefully with water
  7. customThe layers were separated
  8. washthe organics washed with salt brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvents were evaporated
  11. distillationthe product was distilled twice
  12. customrecrystallized from hexane

Sources & evidence

ORD record
ord-76671ff5d64c49e3956b7af86a1f4c05
Source dataset
uspto-grants-2005_11
Patent number
US06960550B2

Reaction notes

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