Tetrakis(triphenylphosphine)palladium(0)

Used Chemicals

• (3-Formylphenyl)boronic Acid [F0445]
• 4-Chliro-3,5-dimethyl-phenol [C0161]
• Tetrakis(triphenylphosphine)palladium(0) [T1350]
• Sodium carbonate [S0560]
• Ethanol

Procedure

(3-Formylphenyl)boronic acid (480 mg, 3.2 mmol) and 4-chloro-3,5-dimethyl-phenol (500 mg, 3.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.048 mmol, 1.5 mol%) were dissolved in degassed ethanol (20 mL). A solution of sodium carbonate (250 mg, 2.4 mmol) in water (5 mL) was added to the solution, and the mixture was stirred for 5 h at 75 °C. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, cooled Et₂O (15 mL) was added and filtered to remove insoluble. The filtrate was concentrated to give the desired product as a pale yellow crystalline solid (506 mg, 2.24 mmol, 70%).

Experimenter's Comments

Ethanol was degassed by purging with N₂.
The reaction mixture was monitored by TLC (hexane : ethyl acetate = 2 : 3, Rf = 0.8).

Analytical Data（4′-Hydroxy-2′,6′-dimethyl-[1,1′-biphenyl]-3-carbaldehyde）

¹H NMR (400 MHz, CDCl₃); δ 10.09 (s, 1H), 8.13 (s, 1H), 7.90 (t, J = 6.8 Hz, 2H), 7.65 (t, J = 7.6 Hz, 1H), 6.56 (s, 2H), 4.79 (s, 1H), 2.36 (s, 6H).

Lead Reference

• Suzuki Reaction for the Synthesis of New Derivatives of 4-Chloro-3,5-Dimethyl Phenol and their in vitro Antibacterial Screening
  • R. H. Zaooli, F. A. Hussein, N. N. A. Jafar, S. N. K. Al-Thamir, Asian J. Chem. 2019, 31, 2955.

References

• W. Shu, Q. Yu, G. Jia, S. Ma, Chem. Eur. J. 2011, 17, 4720.