Hydrochloric Acid → 2-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-propenylselenophene

HRID 1873416Notes

Reaction equation

HRID 1873416 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[Se:29][C:28]([CH:30]=O)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.O.Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([C:25]2[Se:29][C:28]([CH:30]=[CH:1][CH3:2])=[CH:27][CH:26]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 594563315-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)selenophene-2-carbaldehyde

Product 1

HCID 722902632-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-propenylselenophene

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

4.70 g (12.5 mmol) of ethyltriphenylphosphonium bromide are initially introduced in 50 ml of THF at 0° C., and 1.40 g (12.5 mmol) of potassium tert-butoxide dissolved in 30 ml of THF are added. After 1 h, 4.2 g (10.4 mmol) of 5-(2′,3′-difluoro-4′-propoxybiphenyl-4-yl)selenophene-2-carbaldehyde in 100 ml of THF are added, and the batch is stirred at RT for 18 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-(2′,3′-Difluoro-4′-propoxybiphenyl-4-yl)-5-propenylselenophene is obtained as an orange 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-8de603f0432b420795973f529e739fde
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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