6-Bromo-1-methylene-indan → 6-Bromo-1-methyl-indan

HRID 384366Notes

Reaction equation

HRID 384366 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[CH2:11])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 574838316-Bromo-1-methylene-indan

Product 1

HCID 128921496-Bromo-1-methyl-indanYield 62.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-1-methylene-indan 38c (4.91 g, 23.5 mmol) was dissolve in ethyl acetate followed by addition of palladium on carbon (0.98 g). The reaction mixture was reacted at room temperature for 4 hours under hydrogen atmosphere. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 6-bromo-1-methyl-indan 38d (3.11 g, yield 62.7%) as a colourless oil.

Workup

  1. customThe reaction mixture was reacted at room temperature for 4 hours under hydrogen atmosphere
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9beb1587691474f99ee0393307b7958
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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