Trifluoromethylation in a Box

Product No. 802379

Reagents

Compound Catalog No. Equivalents MW Density Amount mmol
Kit Components
Sodium triflinate 743232 3.0 156.06   234 mg 1.50
TBHP solution 458139 5.0 90.12 0.93 0.35 mL 2.50
TPGS-750-M 733857     1.002 1.0 mL  
User Supplied
Heteroaryl [HetArH]   1.0       0.5

Precautions

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.

Procedure

  1. Add the heterocycle (0.50 mmol) into the provided 5-mL reaction vial containing a stir bar and preloaded trifluoromethylating reagent sodium triflinate (234 mg, 1.50 mmol) under N2.
  2. Replace the solid top cap with the provided septum top cap and connect with N2 bubbler through a needle.
  3. Transfer the provided TPGS-750-M/H2O (1.0 mL; 2 wt %) solution into the reaction vial using the provided syringe.
  4. Cool the reaction mixture to ~5 °C and stir for 2-3 minutes.
  5. Add the provided TBHP solution (0.35 mL, 2.50 mmol) slowly at ~5 °C into the reaction vial and stir the resulting mixture vigorously at room temperature until the reaction is complete (monitored by TLC, GC, LC, etc.).
  6. After completion, quench the reaction mixture with saturated NaHCO3 (1 mL) followed by add 1-3 mL of EtOAc (or i-PrOAc) followed by gently stir for 2 minutes and then filter the entire mixture through a bed of silica gel plug (1.5 inch) on a sintered glass Buchner funnel (30 mm diameter).
  7. Wash the silica gel bed with an additional 3 mL of EtOAc (or i-PrOAc) and collect all of the material.
  8. Remove all of the volatiles in vacuo and purify the crude material by flash column chromatography on silica gel.

Notes: Highly crystalline solids must be ground to a fine powder (mortar and pestle) thereby forming a uniform suspension in the aqueous medium prior to introduction of reagents. Slow addition of the TBHP is also necessary. Failure to do so causes clumping, and/or rapid release of sulfur dioxide and ultimately quenching of the CF3 radical to form fluoroform (CHF3).

More information on the research from the Lipshutz Group can be found in the Professor Product Portal.  

Additional information on TPGS–750–M: Second Generation Amphiphile for Organometallic Chemistry in Water at Room Temperature can be found in the Technology Spotlight section of our website.

Materials

     

 

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