Sodium Carbonate → 4-Selenophen-2-ylphenol

HRID 1873423Notes

Reaction equation

HRID 1873423 reaction equation
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC(OC)(C)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>[Se:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 2773454(2-Hydroxyphenyl)boronic acid

Product 1

HCID 126128064-Selenophen-2-ylphenol

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 27.9 g (0.11 mol) of 2-iodoselenophene, 15.0 g (0.11 mol) of 2-hydroxyphenylboronic acid, 6.8 g (5.88 mmol) of tetrakis(triphenylphosphine)palladium(0) and 235 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 19 h. The mixture is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with 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:MTBE=4:1→1:1). Further purification is carried out by digestion in cold n-heptane; 4-selenophen-2-ylphenol is obtained as a beige solid.

Workup

  1. temperatureunder reflux for 19 h
  2. washwashed with water
  3. extractionThe aqueous phase is extracted with MTBE
  4. washthe combined organic phases are washed with sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1→1:1)
  8. customFurther purification

Sources & evidence

ORD record
ord-0758f29e362d49169dbb883bb272b792
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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