Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 10297-05-9, name is 1-Chloro-4-iodobutane, A new synthetic method of this compound is introduced below., name: 1-Chloro-4-iodobutane
817 mg (4.041 mmol) of 5-hydroxypsoralen and 1.413 g (6.47 mmol) of 4-chlorobutyl iodide were refluxed in 80 ml of acetone in the presence of an excess of (3.0 g) anhydrous potassium carbonate for 30 hours. The progress of the reaction was monitored by thin layer chromatography. After 30 hours the reaction mixture was concentrated under reduced pressure and distilled off the solvent almost completely. The oily residue was cooled and diluted with water. The aqueous solution was then acidified with concentrated hydrochloric acid to pH 1. The slurry was stirred for 15-20 min and extracted with 3.x.100 ml of dichloromethane. The dichloromethane layer was extracted with 1.x.25 ml of 1percent sodium hydroxide to separate trace amounts of un-reacted 5-hydroxypsoralen. The dichloromethane layer was washed with 30 ml of 2percent hydrochloric acid and further washed with water to neutral pH. The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated to dryness. The resulting residue was then suspended in petroleum ether and filtered to wash out the excess 4-chlorobutyl iodide. The resulting 5-(4-chlorobutoxy)psoralen was used for the synthesis of various derivatives without further purification. Yield: 1.10 g (92.98percent) Melting point: 115.4-115.6° C. 1H-NMR (500 MHz, CDCl3): delta [ppm]=8.15 (d, 1H, 3J=9.75 Hz, 3-H), 7.60 (d, 1H, 3J=2.62 Hz, 2′-H), 7.17(s, 1H, 8-H), 6.95 (d, 1H, 3J=2.15 Hz, 3′-H), 6.29 (d, 1H, 3J=9.79 Hz, 4-H), 4.52 (t, 2H, 3J=5.44 Hz, 5-OCH2CH2CH2CH2Cl), 3.68 (t, 2H, 3J=5.89 Hz, 5-OCH2CH2CH2CH2Cl), 2.08 (p, 4H, 3J=3.06 Hz, 5-OCH2CH2CH2CH2Cl).; 500 mg (2.473 mmol) of 5-hydroxypsoralen and 893 mg (4.088 mmol) of 4-iodo-1-chlorobutane were stirred at 25° C. in 30 ml of anhydrous acetone in the presence of an excess (2.0 g) of anhydrous potassium carbonate for 28 hours. The progress of the reaction was monitored by thin layer chromatography. After 28 hours the reaction mixture was concentrated under reduced pressure and distilled off the solvent almost completely. The oily residue was cooled and diluted with water. The aqueous solution was then acidified with concentrated hydrochloric acid to pH 1. The slurry was stirred for 15-20 min and filtered. The solids were washed with water to neutral pH and dried. The dried solids were suspended in petroleum ether, filtered and dried under vacuum.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; The Regents of the University of California; US2006/79535; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com