1H-Indene, 2,3-dihydro-1,1,3,3,5-pentamethyl- → HCID 18177854, compound

HRID 394920Notes

Reaction equation

HRID 394920 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4]([CH3:13])([CH3:12])[CH2:3]1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:15][CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2]([CH3:14])([CH3:1])[CH2:3][C:4]2([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 664691H-Indene, 2,3-dihydro-1,1,3,3,5-pentamethyl-HCID 67184N-bromobutanimide

Product 1

HCID 18177854HCID 18177854, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

10.0 g of 1,1,3,3,5-pentamethylindane were dissolved in 125 ml of carbontetrachloride and were added to the resulting solution, 9.92 g of N-bromosuccinimide and 35 mg of 2,2′-azobisisobutyronitrile (AIBN). The reaction mixture was heated to reflux for 5 hours. The reaction was cooled to 0° C. and the succinimide was filtered off. The resulting solution was concentrated in vacuo and the residue (14.7 g) was further dissolved in 150 ml of hexane. The precipitate was again removed by filtration and the solution was concentrated in vacuo, giving 13.8 g of 5-bromomethyl-1,1,3,3-tetramethylindane as a yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. filtrationthe succinimide was filtered off
  4. concentrationThe resulting solution was concentrated in vacuo
  5. dissolutionthe residue (14.7 g) was further dissolved in 150 ml of hexane
  6. customThe precipitate was again removed by filtration
  7. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-067ca15bb01347518ae9026f4b27f31b
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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