chapter 2 palladium catalysts in suzuki cross- coupling reaction

4.4. Purification of the Products
In this study, various types of products were purified by using column
chromatography.
At end of reaction, the catalyst was separated from the reaction mixture by
filtration. Water phase was extracted with ethyl acetate for three times. Organic phase
was dried over sodium sulphate and solvent was removed by using evaporator. Then, it
was extracted with saturated NaCl solution to remove solvent (DMA; N,Ndimethylacetamide).
It must be noted that in the Suzuki reactions of aryl chlorides,
organic phase extracted with HCl (10%) to remove both DMA and tributylamine which
were formed in the course reaction. Products were isolated by using column
chromatography (diameter of column 1.5cm) on silica gel (Merck, Silica Gel 60) with a
0.63mm-0.200mm (20g) or 0.40mm-0.63mm (35g) .
The purity of products was determined through GC, GC/MS and NMR
techniques.
All products are known compounds and products were determined by 1 H NMR,
13
C NMR (Varian AS Mercury + MHz spectrometer) and GC-MS. The values are
represented below and NMR and GC-MS spectrums are given Appendix A and
Appendix B respectively.
4-Acetylbiphenyl: 1 H NMR (400 MHz, CDCl3) δ: 8.01-8.05 (m, 2H), 7.70-7.60
(m, 4H,), 7.50-7.38 (m, 3H), 2.63 (s, 3H); 13 C NMR (100 MHz, CDCl3) δ: 197.9,
146.0, 140.1, 136.1, 129.2, 129.1, 128.5, 127.5, 127.4, 26.8; MS: 196 (M + ), 181, 152.
4-Cyanobiphenyl: 1 H NMR (400 MHz, CDCl3) δ: 7.73-7.66 (m, 4H), 7.60-7.57
(m, 2H), 7.51-7.40 (m, 3H); 13 C NMR (100 MHz, CDCl3) δ: 145.9, 139.4, 132.8, 129.3,
128.9, 128.0, 127.5, 119.1; 111.2; MS: 179 (M + ).
4-Nitrobiphenyl: 1 H NMR (400 MHz, CDCl3) δ: 8.31-8.27 (m, 2H), 7.75-7.71
(m, 2H), 7.64-7.60 (m, 2H); 7.52-7.42 (m, 3H); 13 C NMR (100 MHz, CDCl3) δ: 147.9,
147.3, 139.0, 129.4, 129.1, 128.0, 127.6, 124.3; MS: 199 (M + ), 169, 152, 141.
4-Phenylbenzaldehyde: 1 H NMR (400 MHz, CDCl3) δ: 10.1 (s, 1H, CHO);
7.96 (d, 2H); 7.64 (d, 2H); 7.98 (d, 2H); 7.51-7.42 (m, 3H); 13 C NMR (100 MHz,
CDCl3) δ: 192.1, 147.4, 140.0, 135.5, 130.5, 129.2, 128.7, 127.9, 127.6. MS: 181 (M + ),
152, 76.
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