2,2,2-TRIFLUORO-1-(4-IODO-PHENYL)-ETHANONE Chemical Properties

Boiling point:

260.3±40.0 °C(Predicted)

Density 

1.881±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Colorless to off-white Solid

2,2,2-TRIFLUORO-1-(4-IODO-PHENYL)-ETHANONE Usage And Synthesis

Synthesis

Preparation of the intermediate tert-butyl, 1,1,3,3,3-hexafluoro-2-(4-iodobenzyl)DroDan-2-yloxy)dimethylsilane (1V-1): 4-Iodobenzoic acid methyl ester (5 g, 19.08 mmol) was dissolved in tetrahydrofuran (80 mL) and cooled to 0 °C. (Trifluoromethyl)trimethylsilane (5.43 g, 38.2 mmol) and cesium fluoride (145 mg, 0.954 mmol) were added sequentially. After the addition was completed, the reaction system was slowly warmed to room temperature and stirred continuously for 3 hours. Subsequently, (trifluoromethyl)trimethylsilane (2.715 g, 19.08 mmol) was added additionally and the reaction continued to be stirred at room temperature for 4 hours. After completion of the reaction, the reaction was quenched by the addition of 4M aqueous hydrochloric acid (20 mL) and stirred for 5 hours. The reaction mixture was diluted with ethyl acetate (500 mL), washed sequentially with water (2 x 250 mL), the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a 0% to 10% ethyl acetate/heptane gradient elution to isolate 2,2,2-trifluoro-1-(4-iodophenyl)ethanone (1.8 g, 31% yield), GCMS: m/z = 300, retention time 1.47 min; and 1,1,1,3,3,3-hexafluoro-2-(4-iodophenyl)propan-2-ol (1.6 g, 22% yield), GCMS: m/z = 370, retention time 160 min.

References

[1] Patent: WO2010/86820, 2010, A1. Location in patent: Page/Page column 46
[2] Patent: US2010/197591, 2010, A1. Location in patent: Page/Page column 21

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