(5-CHLORO-2-IODOPHENYL) 2,6-DIFLUOROPHENYL METHANO Chemical Properties

Boiling point:

433.5±45.0 °C(Predicted)

Density 

1.802±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

2-8°C(protect from light)

Appearance

Off-white to light yellow Solid

(5-CHLORO-2-IODOPHENYL) 2,6-DIFLUOROPHENYL METHANO Usage And Synthesis

Synthesis

2-Amino-5-chloro-2,6-difluorobenzophenone (1aa) (2.6 g, 9.7 mmol) was used as a raw material, which was dissolved in acetic acid (10 mL) and concentrated hydrochloric acid (4 mL), and the solution was cooled to 0 °C. A solution of sodium nitrite (NaNO2) (0.7 g, 10.7 mmol) in water (6 mL) was added dropwise while maintaining the temperature at 0-5 °C. After addition, the reaction mixture was stirred at 0 °C for 30 min. Subsequently, cold ethyl acetate (EtOAc) (20 mL) was added dropwise and the solution was stirred for 20 minutes. Next, a solution of iodine (I2) (1.5 g, 5.8 mmol) and potassium iodide (KI) (1.9 g, 11.6 mmol) in water (10 mL) was added drop-wise, and the mixture was slowly warmed to room temperature and stirred for 1 hour. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with saturated sodium thiosulfate (Na2S2O3) aqueous solution (4 x 100 mL). The combined aqueous phases were back-extracted with ethyl acetate (3 x 50 mL). All organic phases were combined and washed sequentially with saturated sodium bicarbonate (NaHCO3) aqueous solution (3×50 mL), water (2×50 mL), dried with anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure to afford the target product (5-chloro-2-iodophenyl)(2,6-difluorophenyl)methanone (2aa) (3.3 g, 90% yield) as a light yellow solid.

References

[1] Patent: US2005/256102, 2005, A1. Location in patent: Page/Page column 141
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 630 - 634
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 27, p. 6598 - 6603
[4] Patent: WO2011/103089, 2011, A1. Location in patent: Page/Page column 39-40

(5-CHLORO-2-IODOPHENYL) 2,6-DIFLUOROPHENYL METHANO(869365-97-9)Related Product Information

• (5-CHLORO-2-IODOPHENYL) 2,6-DIFLUOROPHENYL METHANO
• 2,6-DIFLUOROBENZOPHENONE
• 5-CHLORO-2-IODOTOLUENE
• (2-Fluorophenyl)-(2-iodophenyl)-methanone