1. Honors Project: Organic Chemistry Rebecca Nagurney & Anthony Possanza

2. Objectives  Synthesis of a precursor to an organic molecule with anti-cancer properties  Learn invaluable laboratory skills  Reinforce learning of lecture topics

3.  Component of Turmeric  Indian Spice  Anti-Cancer and Anti- Inflammatory Properties  Synthesis of Derivatives  Acetyl Acetone Curcumin

4. Synthesis of Curcumin

5. Halogenation Using N-Bromosuccinamide (NBS) or N-Chlorosuccinamide (NCS)

6. Chlorination  Chlorinating Reagent:  N-Chlorosuccinamide (NCS)  Reaction:  1.0193g Acetyl Acetone + 1.5094g NCS + 15mL dichloromethane (CH 2 Cl 2 )  Stir reaction for one week at room temperature  Use thin layer chromatography (TLC) to check for product

7. Bromination  Brominating Reagent:  N-Bromosuccinimide (NBS)  Reaction: .5112g Acetyl Acetone +.8342g NBS + 15mL THF (Tetrahydrofuran)  Stir reaction for one week at room temperature  TLC to check for product

8. Thin Layer Chromatography  Solvent system: 10:1 (Hexane: Ethyl Acetate (EtOAc))  Spot  Starting Materials (Acetyl Acetone in EtOH)  Reaction Mixture

9. TLC Continued  Allow solution to run up the TLC plate  Mark the solvent front before removing from the solution  Dry  Dip in 5% Phosphomolybdic Acid in EtOH  Place on hot plate and wait for spots to appear  Calculate Rf Value  Rf = d1/d2  d1 = distance from origin to middle of spot  d2= Distance from origin to solvent front

10. TLC of Bromination Reaction in Tetrahydrofuran (THF)

11. Removing the Solvents  Rotary Evaporator  “Roto Vap”

12. Column Chromatography  Fill column with gel  Load dry or wet  Wet is better!!!  Particles are fine and can get into your lungs!!  Run hexane through the column until the gel is compacted  Pour a layer of sand on top of the compacted gel

14. Column Chromatography  Load product on top of sand  Run hexane through the column and collect samples  Add 25mL Ethyl Acetate to Hexane to increase polarity of the solvent  Increase to a 50% Hexane 50% Ethyl Acetate solution  57 samples were taken

15. TLC of Bromination Reaction in Acetone

16. Results  Reaction in THF  Favors mono-bromo product  Slower moving (more polar) spot on TLC  Reaction in Acetone  Favors di-bromo product  Faster moving (less polar) spot on TLC

17. Future Work  Continuation of honors work into the spring semester  Completion of synthesis of anti-cancer agent  We would like to sincerely thank Dr. Pham for her guidance and support