Hydrochloric Acid → 2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-(pent-1-enyl)selenophene

HRID 1873432Notes

Reaction equation

HRID 1873432 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:19][C:18]([CH:20]=O)=[CH:17][CH:16]=3)=[C:11]([F:22])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].CC(C)([O-])C.[K+].O.Cl.[CH2:31]1[CH2:35]O[CH2:33][CH2:32]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[Se:19][C:18]([CH:20]=[CH:35][CH2:31][CH2:32][CH3:33])=[CH:17][CH:16]=3)=[C:11]([F:22])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 594563395-(4'-Ethyl-3-fluorobiphenyl-4-yl)selenophene-2-carbaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 159628Butyltriphenylphosphonium bromideCatalyst

Procedure

22.0 g (54.5 mmol) of butyltriphenylphosphonium bromide are initially introduced together with 17.3 g (48.4 mmol) of 5-(4′-ethyl-3-fluorobiphenyl-4-yl)selenophene-2-carbaldehyde in 700 ml of THF, and a solution of 6.0 g (53.5 mmol) of potassium tert-butoxide in 100 ml of THF is added with ice-cooling. The mixture is stirred at RT for 3 h. Water and 2 N hydrochloric acid are added, and the batch is extracted with MTBE. The organic phase is washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). 2-(4′-Ethyl-3-fluorobiphenyl-4-yl)-5-(pent-1-enyl)selenophene is obtained as an orange solid.

Workup

  1. temperaturecooling
  2. extractionthe batch is extracted with MTBE
  3. washThe organic phase is washed with sat. sodium chloride soln
  4. customand dried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is purified by column chromatography (SiO2, toluene)

Sources & evidence

ORD record
ord-3fdc39126f79436bb8078e28aa717480
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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