Sodium Carbonate → 2-(4'-Ethyl-3-fluorobiphenyl-4-yl)selenophene

HRID 1873427Notes

Reaction equation

HRID 1873427 reaction equation
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=2)[CH:11]=[CH:12][C:13]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[CH2:23]([C:20]1[CH:19]=[CH:18][C:17]([C:10]2[CH:11]=[CH:12][C:13]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([F:7])[CH:9]=2)=[CH:22][CH:21]=1)[CH3:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 534025754'-Ethyl-3-fluorobiphenyl-4-boronic acid

Product 1

HCID 594563342-(4'-Ethyl-3-fluorobiphenyl-4-yl)selenophene

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 34.2 g (0.16 mol) of 2-bromoselenophene, 40.0 g (0.16 mol) of 3-fluoro-4′-ethylbiphenyl-4-ylboronic acid, 10.0 g (8.65 mmol) of tetrakis-(triphenylphosphine)palladium(0) and 200 ml of 2 N sodium carbonate soln. in 500 ml of toluene/ethanol (2:3) is heated at 90° C. for 2 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with water, and the solution is dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1). 2-(4′-Ethyl-3-fluorobiphenyl-4-yl)-selenophene is obtained as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with water
  5. customthe solution is dried
  6. concentrationThe solution is concentrated to dryness
  7. customthe residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1)

Sources & evidence

ORD record
ord-b74f375a4d89404897a55cbadbb82001
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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