2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-(pent-1-enyl)selenophene → HCID 59456308, compound

HRID 1873433Notes

Reaction equation

HRID 1873433 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]=[CH:21][CH2:22][CH2:23][CH3:24])=[CH:18][CH:19]=3)=[C:11]([F:25])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[Se:16][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:18][CH:19]=3)=[C:11]([F:25])[CH:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 722902452-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-(pent-1-enyl)selenophene

Product 1

HCID 59456308HCID 59456308, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

17.1 g (43.0 mmol) of 2-(4′-ethyl-3-fluorobiphenyl-4-yl)-5-(pent-1-enyl)-selenophene are hydrogenated in 170 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=98:2→95:5). The further purification is carried out by recrystallisation from ethanol and n-heptane. 2-(4′-Ethyl-3-fluorobiphenyl-4-yl)-5-pentylselenophene is obtained as a colourless solid (m.p. 52° C.).

Workup

  1. filtrationis filtered
  2. concentrationconcentrated to dryness
  3. customthe crude product is purified by column chromatography (SiO2, n-heptane:toluene=98:2→95:5)
  4. customThe further purification
  5. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-b6ceb9fb80a94c048b1c8ceff5c4d35b
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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