SUZUKI+Lab+Report

Akira Suzuki originally published the Suzuki reaction in 1979. Suzuki received the 2010 Nobel Prize in Chemistry for the discovery and formation of the Suzuki reaction. This reaction is also known as Suzuki-Miyaura reaction and Suzuki Coupling. The fundamentals of the Suzuki reaction involve organometallic chemistry, which is the study of compounds containing bonds between carbon and metal. Lithium and Grignard reagents are a familiar example of organometallic chemistry. The general process of combining two separate hydrocarbon pieces with the help of a metal catalyst is called coupling. The significance of this coupling creates carbon-carbon bonds. The Suzuki reaction involves cross-coupling of two different chemical compounds versus the coupling of identical compounds known as homo-coupling. Aryl is any functional group substituent derived from a simple aromatic ring, this compound is one of the reactants in the Suzuki reaction the other reactant is a vinyl-halide, which is a vinyl groups with a formula of –CH=CH2 that contains a halide. Vinyl resembles the chemical formula of ethene, however a functional group replaces one of the hydrogen characterizing a vinyl. Palladium (0) complex is the metal catalyst that aids in binding of these two compounds. Palladium (0) complex must be made in situ from PdCl2 or Pd(OAc)2. Triphenylphosphine and palladium with a base and an isopropanol (aq) solvent can also be used. This experiment exchanges the isopropanol solvent for water and the in situ formation of palladium for palladium on carbon. This trade reduces the cost of the experiment and the hazards to humans and the environment. Water is free and much greener than the organic solvent that previously is used. This experiment still provides the conditions that produce 4-phenylphenol while satisfying many the 12 green chemistry principle.
 * Introducton:**

1) In a fume hood, place the following in a 50-ml round bottom flask: Phenylboronic acid (122 mg); potassium carbonate (415 mg); 4-iodophenol (220 mg); and water (10.0 ml) 2) Add about 1 ml of water to the vial of 10% palladium on carbon, this will create a suspension. Transfer the suspension to the reaction flask. 3) Heat the mixture vigorously under reflux for 30 minutes, using a sand bath as the heat source, stir the reaction often. A solid may precipitate. 4) Remove flask from the sand bath and allow cooling to room temperature. 5) Add aqueous HCL (2 M) to the filtrate until acidic to litmus paper. Stir very well after adding the HCL as the solid acts as a sponge and will 'soak up' the acid. Collect the crude product via vacuum filtration (Hirsch funnel) and wash with water (10 ml). 6) Disolve the collected solid in about 10 ml of methanol (25 ml Erlenmeyer flask) and remove the Pd/C by gravity filtration (collect in 50 ml Erlenmeyer). 7) Add about 10 ml of distilled water to the crude product disolved in methanol, this will cause a solid to precipitate out. Heat until entire product has dissolved into solution. Once dissolved, allow cooling to room temp and then place in an ice bath. 8) collect recrystalized product via vacuum filtration (Hirsch funnel) and dry very thoroughly (can be left until following lab period). Remove solid from the funnel, weigh and take the melting point and IR spectrum. Division of Chemical Education www.ICE.DirCHED.org Vol. 85 No. 4 April 2008. Journal of Chemical Education "Greening Up" the Suzuki Reaction
 * Procedure:**




 * Data:**

Product mass = 0.116g Product melting point = 164.4-168.6 C Actual melting point= 163-167 C The product was pearl coloured with a mother of pearl sheen to it.
 * Compound || GMW || Amount Added || mmol || mp (C) ||
 * phenylboronic acid || 121.93 || 122mg || 1.00 || 216-219 ||
 * 4-iodophenol || 220.01 || 220mg || 1.00 || 92-94 ||
 * potassium carbonate || 138.21 || 415mg || 3.00 || 891 ||
 * 10% palladium carbonate || 106.42 || 3mg ||  ||   ||
 * 2 M HCl || 36.46 || 50 drops ~2.5ml ||  ||   ||
 * methanol || 32.04 || 10ml ||  || -98 ||

During the reflux portion the procedure calls for rapid stirring, however the sand baths are not stir bar friendly, this was circumnavigated by manual stirring. While adding the HCL be sure to mix extreemly well after each drop, the product acts like a sponge and will give conflicting results on litmus paper. While removing the Pd/C it is wise to set up a double filter paper system, as the particles are so fine they can pass through a single piece of filter paper. This can also be over come by repeating the filtration process multiple times. The reaction is very well known and it is benificial to students to be able to do it at an undergraduate level. The melting point of the product corresponds to the actual melting point, this is a good indication of the purity of the product. The IR spectrum has a major peak at 3422.26 indicating an alcohol, the peak is not a regular shape for an alcohol. However, this could be the result of a scale manipulation. There is a peak at around 3100, while it is not very prominent, it indicates an sp2 hybridized carbon-hydrogen bond. This reaction is considered green because; water is used as the solvent, it uses Pd/C as a catalyst. This reaction allows for the creation of carbon carbon sigma bonds using a green solvent. This is the starting block for most organic synthesis. In this reaction the phenylboronic acid is coupled with the 4-iodophenol, using 10% Pd/C as the catalyst forming 4-phenylphenol, whis is used as a non-steroidal anti-inflammatory drug.
 * IR Spectrum:**
 * Notes;**
 * Conclusion:**

Thanks for writing another nice report. Format (2/2) Style (2/2) Data (3/3) quality of result (1/1) quality of reported data (1/1) conclusion (2/2) error (1/1) total: 14.