Potassium Carbonate → 1~3~,1~5~,2~2~-Trifluoro-3~4~-propyl-1~1~,2~1~:2~4~,3~1~-terphenyl

HRID 713377Notes

Reaction equation

HRID 713377 reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH3:31])=[CH:25][CH:24]=2)[CH:20]=[CH:19][C:18]=1B(O)O>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:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:19]=[CH:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH3:31])=[CH:25][CH:24]=3)=[CH:22][C:17]=2[F:16])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1363131-Bromo-3,5-difluorobenzeneHCID 53402576(3-Fluoro-4'-propyl[1,1'-biphenyl]-4-yl)boronic acid

Product 1

HCID 595924131~3~,1~5~,2~2~-Trifluoro-3~4~-propyl-1~1~,2~1~:2~4~,3~1~-terphenyl

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere, a suspension solution containing 3,5-difluorobromobenzene (71 g), potassium carbonate (75 g), tetrakis(triphenylphosphine)palladium (0) (2.2 g), and ethanol (250 mL) was heated to 70° C., and a solution in which 2-fluoro-4-(4-propylphenyl)phenylboronic acid (100 g, prepared by a method disclosed in EP 2123623) had been dissolved in ethanol (200 mL) was dropped thereinto. Then, the resulting solution was stirred at 70° C. for 5 hours. The solution was cooled with ice and filtered to separate precipitated crystals and an inorganic salt, the obtained solid was dissolved in a solution containing hexane and toluene (4:1), and then the solution was purified by silica gel column chromatography. The purified product was recrystallized from ethanol to yield 18.7 g of 3,5-difluoro-[2-fluoro-4-(4-propylphenyl)phenyl]benzene.

Workup

  1. additionwas dropped
  2. temperatureThe solution was cooled with ice
  3. filtrationfiltered
  4. customto separate
  5. customprecipitated crystals
  6. dissolutionan inorganic salt, the obtained solid was dissolved in a solution
  7. additioncontaining hexane and toluene (4:1)
  8. customthe solution was purified by silica gel column chromatography
  9. customThe purified product was recrystallized from ethanol

Sources & evidence

ORD record
ord-e8bb97b486ef4297904f5351fe9782fe
Source dataset
uspto-grants-2015_11
Patent number
US09181484B2

Reaction notes

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