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

HRID 1873434Notes

Reaction equation

HRID 1873434 reaction equation
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[C:13]([F:14])=[C:12](B(O)O)[CH:11]=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=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>[CH2:24]([C:21]1[CH:22]=[CH:23][C:18]([C:9]2[CH:10]=[CH:11][C:12]([C:2]3[Se:3][CH:4]=[CH:5][CH:6]=3)=[C:13]([F:14])[C:8]=2[F:7])=[CH:19][CH:20]=1)[CH3:25]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1370132-BromoselenopheneHCID 184694332,3-Difluoro-4'-ethylbiphenyl-4-ylboronic acid

Product 1

HCID 594562952-(4'-Ethyl-2,3-difluorobiphenyl-4-yl)selenophene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 56.0 g (0.27 mol) of 2-bromoselenophene, 70.0 g (0.27 mol) of 2,3-difluoro-4′-ethylbiphenyl-4-ylboronic acid, 22.0 g (19.0 mmol) of tetrakis(triphenylphosphine)palladium(0) and 800 ml of 2 N sodium carbonate soln. in 2.5 l of toluene/ethanol (1:1) is heated at 90° C. for 17 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, toluene). The further purification is carried out by recrystallisation from ethanol and n-heptane. 2-(4′-Ethyl-2,3-difluorobiphenyl-4-yl)-selenophene is obtained as a yellowish 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, toluene)
  8. customThe further purification
  9. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-8454be194d104d5eb45a02209f4523d5
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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