Hydrochloric Acid → 2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-vinylselenophene

HRID 1873430Notes

Reaction equation

HRID 1873430 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].[CH3:23]C(C)([O-])C.[K+].O.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[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]=[CH2:23])=[CH:17][CH:16]=3)=[C:11]([F:22])[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

5.0 g (13.9 mmol) of methyltriphenylphosphonium bromide are initially introduced together with 4.20 g (11.8 mmol) of 5-(4′-ethyl-3-fluorobiphenyl-4-yl)selenophene-2-carbaldehyde in 180 ml of THF, and a solution of 1.50 g (13.4 mmol) of potassium tert-butoxide in 20 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-vinylselenophene is obtained as a beige 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-242725c20fe84e0b9418365c6c7bd641
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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