2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-vinylselenophene → 2-Ethyl-5-(4'-ethyl-3-fluorobiphenyl-4-yl)selenophene

HRID 1873431Notes

Reaction equation

HRID 1873431 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[Se:16][C:17]([CH:20]=[CH2:21])=[CH:18][CH:19]=3)=[C:11]([F:22])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:20]([C:17]1[Se:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)=[CH:10][C:11]=2[F:22])=[CH:19][CH:18]=1)[CH3:21]

Participants

4

Reactant 1

HCID 594563562-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-vinylselenophene

Product 1

HCID 594562592-Ethyl-5-(4'-ethyl-3-fluorobiphenyl-4-yl)selenophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.10 g (8.73 mmol) of 2-(4′-ethyl-3-fluorobiphenyl-4-yl)-5-vinylselenophene are hydrogenated in 30 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-Ethyl-5-(4′-ethyl-3-fluorobiphenyl-4-yl)selenophene is obtained as a colourless solid (m.p. 110° 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-28c3632568d944baa9868fafec175fbe
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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