Sodium Carbonate → 2-(4-Trifluoromethoxyphenyl)selenophene

HRID 1873391

Reaction equation

HRID 1873391 reaction equation
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]([F:20])([F:19])[O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[F:7][C:8]([F:19])([F:20])[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[Se:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 594563432-(4-Trifluoromethoxyphenyl)selenophene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 15.1 g (58.7 mmol) of 2-iodoselenophene, 13.9 g (67.7 mmol) of 4-trifluoromethoxyphenylboronic acid, 3.90 g (3.38 mmol) of tetrakis(triphenylphosphine)palladium(0) and 150 ml of 2 N sodium carbonate soln. in 400 ml of toluene/ethanol (1:1) is heated under reflux for 23 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted a number of times with MTBE. The combined organic phases are washed with 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→10:1→1:1). Further purification is carried out by recrystallisation from n-heptane; 2-(4-trifluoromethoxyphenyl)selenophene is obtained as a yellowish solid.

Workup

  1. temperatureunder reflux for 23 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted a number of times with MTBE
  5. washThe combined organic phases are washed with 1 N hydrochloric acid and sat. sodium chloride soln
  6. customThe solution is dried
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=20:1→10:1→1:1)
  9. customFurther purification
  10. customis carried out by recrystallisation from n-heptane

Sources & evidence

ORD record
ord-2b592262881749ea9867081798fb2204
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Linked notes

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