Sodium Carbonate → HCID 59456280, compound

HRID 1873440Notes

Reaction equation

HRID 1873440 reaction equation
Br[C:2]1[Te:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([F:19])[C:11]=1[F:20])[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[Te:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([F:19])[C:11]=1[F:20])[CH3:8]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1436042-BromotelluropheneHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acid

Product 1

HCID 59456280HCID 59456280, compound

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 10.0 g (38.7 mmol) of 2-bromotellurophene, 8.0 g (39.6 mmol) of 4-ethoxy-2,3-difluorophenylboronic acid, 3.5 g (3.0 mmol) of tetrakis-(triphenylphosphine)palladium(0) and 100 ml of 2 N sodium carbonate soln. in 200 ml of toluene/ethanol (1:1) is heated under reflux for 1.5 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with 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:toluene=3:2). Further purification is carried out by recrystallisation from ethanol; 2-(4-ethoxy-2,3-difluorophenyl)tellurophene is obtained as a yellow solid.

Workup

  1. temperatureunder reflux for 1.5 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic phases are washed with sat. sodium hydrogencarbonate soln
  6. customThe solution is dried
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by column chromatography (SiO2, n-heptane:toluene=3:2)
  9. customFurther purification
  10. customis carried out by recrystallisation from ethanol

Sources & evidence

ORD record
ord-1018220a9c224507b8c78d8d6affab89
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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