Adding a certain compound to certain chemical reactions, such as: 17024-12-3, name is 9-Iodophenanthrene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 17024-12-3, SDS of cas: 17024-12-3
A 500 mL three-necked round-bottomed flask equipped with a mechanical stirrer, reflux condenser, and inert gas in- and outlet was charged with quinidine (QD-1, 12.8g, 39.5 mmol, 1.2 eq). The flask was flushed for 30 min with a gentle stream of argon. Anhydrous dimethyl sulfoxide (130 mL, freshly distilled in presence of CaHz) was added, and the reaction mixture was stirred at room temperature until all the quinidine was dissolved. Sodium hydride (60% oil dispersion, 2.0g, 1.5 eq. ) was added in small portions yielding an orange, slightly cloudy solution of the corresponding sodium alkoxide. Upon addition of pyridine (6.4 mL, 2.4 eq. ) and copper (I) g, 1.2 eq. ) to the reaction mixture at room temperature, the color of the reaction mixture was changed from orange to dark green. After 30 min all of the precipitate dissolved, and a clear solution was formed. 9- iodophenanthrene (10.0 g, 32.9 mmol), was added, and the reaction mixture was kept at 113 C for 70 h (oil bath, temperature: 120 C). The reaction mixture was allowed to cool to room temperature. Water (100 mL), methylene chloride(100 mL), and diethyl ether (100 mL) were successively added to the brown solution followed by ethylenediaminetetraacetate disodium salt dehydrate (20 g) and concentrated aqueous ammonia solution (20 mL, 29%, w/w). The argon inlet was removed, and a gentle stream of air was flushed through the well-agitated reaction mixture for about 1 h. The reaction mixture was transferred to a separatory funnel and the turquoise blue aqueous phase separated from the dark brown organic phase. The aqueous layer was washed twice with methylene chloride (100 mL), and the combined organic phases were extracted three times with aqueous ammonia solution (200 mL, 5%, w/w) until the aqueous phase remained colorless. Then the organic layer was washed with HCl aq (1 N 2 x 50 mL) twice and washed with H20 three times (3 x 50 mL) to remove the left QD. The organic layer was washed with NH40H to neutralize the salt and dried over Na2S04 and the solvent was removed in vacuo to yield the crude product. The crude product was dissolved in ethyl ether (300 mL) and treated with HCI (IN in Et20) until no further precipitates was generated. The precipitates were collected and dissolved in CH2C12 and basified with NH40H and dried over Na2S04 and the solvent in vacuo to give yellowish foam QD-PHN (5.6g, 66% yield). [alpha]D23 = + 310.7(C 0.89 EtOH) (at)HNMR (CDC13, 400 Hz) 6 8.65-8.71 (m, 2H), 8.61 (d, J = 4.8 Hz, 1H), 8.52(d, J = 8 Hz, 1H), 8.07 (d, J= 9.2 Hz, 1H), 7.70-7.75 (m, 2H), 7.55 (d, 2.4 Hz, 1H), 7.38-7.46(m, 5H), 6.66 (s, 1H), 6.35 (br, 1H), 6.12-6.21 (m, 1H), 5.18(d, J=10.4 Hz, 1H), 5.12 (m, 1H), 4.03 (s, 3H), 3.32-3.42 (m, 2.97-3.06 (m, 2.79-2.87 (m, 1H),2.44-2.50(t, J= 10 Hz, 1H), 2.34-3.25 (m, 1H), 1.97 (br, 1H), 1.55-1.62 (m, 3H). ยน3CNMR:(CDCl3, 100Hz): 158.1, 150.4, 147.71, 144.7, 143.7, 140.3, 132.3, 132.2, 131.5, 127.5,127.3, 126.8, 126.7, 126.6,126.4, 124.5,122.8, 122.7,122.3, 121.8, 118.2, 114.7, 104.8, 100.8, 78.8, 60.5, 55.8, 50.2, 49.9, 39.6, 27.8, 26.5, 22.1. IR: 3062, 2935, 2863, 1622, 1594, 1507, 1454, 1226, 1117, 750.
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Reference:
Patent; BRANDEIS UNIVERSITY; WO2005/121137; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com