Potassium Carbonate → 3-Fluoro-4'-propylbiphenyl

HRID 2260902Notes

Reaction equation

HRID 2260902 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].Br[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[F:20][C:16]1[CH:15]=[C:14]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 140821-Bromo-3-fluorobenzeneHCID 4100861(4-Propylphenyl)boronic acid

Product 1

HCID 185211083-Fluoro-4'-propylbiphenylYield 80.6%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

Into a reaction vessel under an atmosphere of nitrogen, 4-propyl phenylboronic acid (T16; 200.0 g), 1-bromo-3-fluorobenzene (T8; 177.8 g), potassium carbonate (281.9 g), Pd(Ph3P)2Cl2 (7.2 g), toluene (600 ml), and Solmix A-11 (600 ml) were put and heated under reflux for 2 hours. After the reaction mixture had been cooled to 25° C., the solution was poured into water (2,000 ml) and toluene (1,000 ml), and mixed. The mixture was then allowed to stand to be separated into two layers of an organic layer and an aqueous layer. Extraction into an organic layer was carried out and the resulting organic layer was fractionated. The extracts were washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by means of fraction-collecting column chromatography using heptane as the eluent and silica gel as the stationary phase powder. The solution was further purified by recrystallization from Solmix A-11 and then dried, whereby 175.5 g of 3-fluoro-4′-propylbiphenyl (T17) was obtained. The yield based on the compound (T8) was 80.3%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. additionmixed
  4. customto be separated into two layers of an organic layer
  5. extractionExtraction into an organic layer
  6. washThe extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe resulting solution was concentrated under reduced pressure
  9. customthe residue was purified by means
  10. customof fraction-collecting column chromatography
  11. customThe solution was further purified by recrystallization from Solmix A-11
  12. customdried

Sources & evidence

ORD record
ord-748b112e6ada4a7e9ddd25cdd65008f6
Source dataset
uspto-grants-2010_12
Patent number
US07846514B2

Reaction notes

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