Hydrochloric Acid → 2-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

HRID 1873438Notes

Reaction equation

HRID 1873438 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].[CH2:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[Se:42][C:41]([CH:43]=O)=[CH:40][CH:39]=3)=[C:34]([F:45])[C:33]=2[F:46])=[CH:28][CH:27]=1)[CH3:25].CC(C)([O-])C.[K+].Cl>C1COCC1.O>[CH:43]([C:41]1[Se:42][C:38]([C:35]2[CH:36]=[CH:37][C:32]([C:29]3[CH:30]=[CH:31][C:26]([CH2:24][CH3:25])=[CH:27][CH:28]=3)=[C:33]([F:46])[C:34]=2[F:45])=[CH:39][CH:40]=1)=[CH:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80374Propyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 59456278HCID 59456278, compound

Product 1

HCID 722902622-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4.8 g (12.0 mmol) of propyltriphenylphosphonium bromide are initially introduced together with 3.60 g (9.56 mmol) of 5-(4′-ethyl-2,3-difluoro-biphenyl-4-yl)selenophene-2-carbaldehyde in 180 ml of THF, and a solution of 1.30 g (11.6 mmol) of potassium tert-butoxide in 20 ml of THF is added with ice-cooling. The mixture is stirred at RT for 1 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, n-heptane:toluene=95:5). 2-But-1-enyl-5-(4′-ethyl-2,3-difluorobiphenyl-4-yl)selenophene is obtained as a yellow 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, n-heptane:toluene=95:5)

Sources & evidence

ORD record
ord-d2ff46c953834ec5af1911c0be0761b4
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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