2-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene → 2-Butyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

HRID 1873439Notes

Reaction equation

HRID 1873439 reaction equation
[CH:1]([C:5]1[Se:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=3)=[C:12]([F:24])[C:11]=2[F:25])=[CH:8][CH:9]=1)=[CH:2][CH2:3][CH3:4]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:5]1[Se:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=3)=[C:12]([F:24])[C:11]=2[F:25])=[CH:8][CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 722902622-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

Product 1

HCID 594562702-Butyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.40 g (5.72 mmol) of 2-but-1-enyl-5-(4′-ethyl-2,3-difluorobiphenyl-4-yl)-selenophene are hydrogenated in 25 ml of ethyl acetate, in the presence of Pd/C (5% of Pd) at atmospheric pressure and RT. The reaction soln. is filtered and concentrated to dryness, and the crude product is purified by column chromatography (SiO2, n-heptane:toluene=9:1). The further purification is carried out by recrystallisation from ethanol and n-heptane. 2-Butyl-5-(4′-ethyl-2,3-difluorobiphenyl-4-yl)selenophene is obtained as a colourless solid (m.p. 73° C.).

Workup

  1. filtrationis filtered
  2. concentrationconcentrated to dryness
  3. customthe crude product is purified by column chromatography (SiO2, n-heptane:toluene=9:1)
  4. customThe further purification
  5. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-d4501e35a5b645d881d3747aa8b87b8a
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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