Potassium Carbonate → 3-Fluoro-4'-propylbiphenyl

HRID 1406826Notes

Reaction equation

HRID 1406826 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1>C1COCC1>[F:17][C:18]1[CH:19]=[C:20]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1363741-Bromo-4-propylbenzeneHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 185211083-Fluoro-4'-propylbiphenylYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a nitrogen atmosphere, a solution prepared by mixing 50.00 g of 4-propylbromobenzene, 0.87 g of tetrakis-triphenylphosphine palladium, 60 mL of an aqueous potassium carbonate solution (2 mol/L), and 150 mL of THF was heated to 60° C., and 35.14 g of 3-fluorophenylboronic acid was added to the solution over 20 minutes. After the resultant mixture was stirred at 60° C. for 3 hours, the mixture was allowed to cool, and an organic layer was separated by adding hexane. The organic layer was washed with saturated brine and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. As a result of purification by silica gel column chromatography, 44.32 g of 3-fluoro-1-(4-propylphenyl)benzene was produced.

Workup

  1. customIn a nitrogen atmosphere, a solution prepared
  2. temperatureto cool
  3. customan organic layer was separated
  4. additionby adding hexane
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. additionby adding sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customAs a result of purification by silica gel column chromatography

Sources & evidence

ORD record
ord-4168fa2b6b7049a4848e4d0929345adb
Source dataset
uspto-grants-2014_12
Patent number
US08916718B2

Reaction notes

Loading…