Water → 2-[4-(4-Propylcyclohexyl)phenyl]selenophene

HRID 1873386

Reaction equation

HRID 1873386 reaction equation
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 31047104-(trans-4-Propylcyclohexyl)phenylboronic Acid

Product 1

HCID 594562962-[4-(4-Propylcyclohexyl)phenyl]selenophene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

A mixture 0111.0 g (41.1 mmol) of 2-iodoselenophene, 7.98 g (32.4 mmol) of 4-(4-propylcyclohexyl)phenylboronic acid, 3.70 g (3.20 mmol) of tetrakis(triphenylphosphine)palladium(0) and 60 ml of 2 N sodium carbonate soln. in 160 ml of toluene/ethanol (1:1) is heated under reflux for 22 h. After cooling, water is added, and the batch is extracted a number of times with MTBE. The combined organic phases are washed with water, sat. sodium hydrogencarbonate soln., 1 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:EtOAc=20:1). The further purification is carried out by recrystallisation from n-heptane; 2-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as a colourless solid.

Workup

  1. temperatureunder reflux for 22 h
  2. temperatureAfter cooling
  3. extractionthe batch is extracted a number of times with MTBE
  4. washThe combined organic phases are washed with water, sat. sodium hydrogencarbonate soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=20:1)
  8. customThe further purification
  9. customis carried out by recrystallisation from n-heptane

Sources & evidence

ORD record
ord-76e1073097df4d6c889c3db6f8abdc88
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Linked notes

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