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

HRID 1943516Notes

Reaction equation

HRID 1943516 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[S: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:24](C)([O-])C.[K+].O.Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[S:19][C:18]([CH:20]=[CH:23][CH3:24])=[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 581606825-(4'-Ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

Product 1

HCID 670675042-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-propenylthiophene

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

26.0 g (70.0 mmol) of ethyltriphenylphosphonium bromide are initially introduced in 400 ml of THF together with 20.0 g (62.6 mmol) of 5-(4′-ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde, and a solution of 7.86 g (70.0 mmol) of potassium tert-butoxide in 100 ml of THF is added with ice-cooling. The mixture is stirred at room temperature for 20 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 solution and dried using sodium sulfate. The solution is evaporated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:toluene 9:1→toluene).

Workup

  1. temperaturecooling
  2. extractionthe batch is extracted with MTBE
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. customdried
  5. customThe solution is evaporated to dryness
  6. customthe residue is purified by column chromatography (SiO2, n-heptane:toluene 9:1→toluene)

Sources & evidence

ORD record
ord-62267da294d043da953d384abbb06a52
Source dataset
uspto-grants-2013_03
Patent number
US08394293B2

Reaction notes

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