2-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-vinylselenophene → 2-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-ethylselenophene

HRID 1873415Notes

Reaction equation

HRID 1873415 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[Se:20][C:21]([CH:24]=[CH2:25])=[CH:22][CH:23]=2)=[CH:15][CH:14]=1>C(OCC)(=O)C.C1(C)C=CC=CC=1.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[Se:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 594562742-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-vinylselenophene

Product 1

HCID 594562762-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-ethylselenophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584019Toluene ethylacetateSolvent

Procedure

3.0 g (5.0 mmol) of 2-(2′,3′-difluoro-4′-propoxybiphenyl-4-yl)-5-vinylselenophene are hydrogenated in 90 ml of ethyl acetate/toluene (2:1), in the presence of Pd/C (5% of Pd) at atmospheric pressure and RT. The reaction soln. is filtered and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane:toluene=2:1). The further purification is carried out by recrystallisation from n-heptane. 2-(2′,3′-Difluoro-4′-propoxybiphenyl-4-yl)-5-ethylselenophene is obtained as a solid having an m.p. of 126° C.

Workup

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

Sources & evidence

ORD record
ord-14e189ea25aa44b489e3b51ea1bc5642
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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