6-Bromo-1-ethylidene-indan → 6-Bromo-1-ethyl-indan

HRID 384373Notes

Reaction equation

HRID 384373 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[CH:11][CH3:12])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 686133646-Bromo-1-ethylidene-indanHCID 178418361HCID 178418361, compound

Product 1

HCID 574838336-Bromo-1-ethyl-indanYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-1-ethylidene-indan 41a (3.07 g, 13.7 mmol) was dissolved in 80 mL of ethyl acetate followed by addition of palladium on carbon (0.61 g) at room temperature. The mixture was hydrogenated for 5 hours in a hydrogenator under 3 atm. of hydrogen. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered to remove palladium on carbon and the filter cake was washed with ethyl acetate (10 mL×3). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound 6-bromo-1-ethyl-indan 41b (2.75 g, 88.7%) as a light yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove palladium on carbon
  3. washthe filter cake was washed with ethyl acetate (10 mL×3)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4bfee9bd64bd4d9a86b81aac224a4014
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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