Hydrochloric Acid → 2-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene

HRID 1873401Notes

Reaction equation

HRID 1873401 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH2:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[Se:43][C:42]([CH:44]=O)=[CH:41][CH:40]=2)=[C:35]([F:46])[C:34]=1[F:47])[CH3:31].Cl>C1COCC1.O>[CH2:30]([O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[Se:43][C:42]([CH:44]=[CH:2][CH2:3][CH3:4])=[CH:41][CH:40]=2)=[C:35]([F:46])[C:34]=1[F:47])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80374Propyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 594563155-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde

Product 1

HCID 722902482-(4-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

14.1 g (35.0 mmol) of propyltriphenylphosphonium bromide are initially introduced in 150 ml of THF at 0° C., and 3.93 g (35.0 mmol) of potassium tert-butoxide dissolved in 50 ml of THF are added. After 1 h at this temperature, 9.0 g (28.6 mmol) of 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde are added as a solution in 300 ml of THF, and the batch is stirred at RT for 19 h. Water and 2 N hydrochloric acid are added to the mixture, and the batch is extracted with MTBE. The combined organic phases are 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-Ethoxy-2,3-difluorophenyl)-5-but-1-enylselenophene is obtained as a reddish solid.

Workup

  1. additionare added
  2. extractionthe batch is extracted with MTBE
  3. washThe combined organic phases are 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-abd2f197ce8b460f9cbfa4ef98e825ba
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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