Toluene → HCID 57823325, compound

HRID 2352746Notes

Reaction equation

HRID 2352746 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>[Pd].O.C(O)C>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:19]3[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[CH:18]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH3:15]

Participants

8

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 232384604-Bromo-4'-ethyl-1,1'-biphenyl

Product 1

HCID 57823325HCID 57823325, compoundYield 145.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5.6 g (21.4 mmol) of 4-bromo-4′-ethylbiphenyl, 3.6 g (25.7 mmol) of 3-fluorophenyl dihydroxyborane, 4.4 g (32.2 mmol) of potassium carbonate, 0.3 g of 5%-Pd/C and 60 mL of a mixed solvent of toluene, ethanol and water (ratio: 1/1/1) was refluxed for 6 hours to obtain a reaction solution. After removing the catalyst by filtration, 50 mL of toluene was added to the reaction solution, which was then washed with water. The reaction solution having been washed with water was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the reaction solution under reduced pressure to obtain 8.6 g of a residue. The residue was purified by silica gel column chromatography (eluent: heptane/toluene=4/1) to obtain 5.1 g of crude crystals of the compound (E-8). The crude crystals were dissolved in a mixed solvent of ethanol and ethyl acetate (ratio: 10/1) and recrystallized therefrom to obtain 4.5 g of purified crystals of the compound (E-8).

Workup

  1. temperaturewas refluxed for 6 hours
  2. customto obtain a reaction solution
  3. customAfter removing the catalyst
  4. filtrationby filtration, 50 mL of toluene
  5. additionwas added to the reaction solution, which
  6. washwas then washed with water
  7. washThe reaction solution having been washed with water
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off from the reaction solution under reduced pressure

Sources & evidence

ORD record
ord-0c130930e19648e8a0ef1061eacc59b4
Source dataset
uspto-grants-2010_07
Patent number
US07749403B2

Reaction notes

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