Some common heterocyclic compound, 18648-66-3, name is 2-(4-Bromophenyl)-1,1-diphenylethylene, molecular formula is C20H15Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C20H15Br
(1) Synthesis of 2-(2-biphenylyl)-9,10-bis(4-(2,2-diphenylvinyl)phenyl)-9,10-dihydroxy-9,10-dihydro anthracene; [Compound (B1-0)]; Under an atmospheric argon gas flow, 4-(2,2-diphenylvinyl)-1-bromobenzene in an amount of 9.8 g (29 mmol, 3 eq) was dissolved into a mixed solvent of anhydrous toluene in an amount of 45 milliliter and anhydrous THF in an amount of 45 milliliter, followed by cooling down to the temperature of – 20 C by means of dry ice / methanol bath. Adding hexane solution of n-butyllithium in an amount of 19 milliliter (1.59 mol/litter, 30 mmol; 1.04 eq), the resultant solution was stirred at the temperature of -20 C for 1 hour. Into the resultant solution, 2-(2-biphenylyl)-9,10-anthraquinone [Compound (A)] in an amount of 3.5 g (9.7 mmol) was added and after stirring at the room temperature for 2 hours, it was stood alone for a night. The resultant reaction mixture was deactivated with the use of saturated ammonium chloride aqueous solution in an amount of 50 milliliter, and the resultant solid was separated. The solid was washed use of the mixed solvent of hexane : dichloromethane = 1:1 (capacity ratio) and as a result, 5.0 g of white solid compound was obtained (yield: 59 %). The white solid was identified as the Compound (B1-0) in accordance with 1H-NMR. The measurement results of 1 H-NMR are shown as the following: 1H-NMR (CDCl3, TMS) delta 2.17 (1H, s), 2.66 (1H, s), 6.21 (2H, d, J=8Hz), 6.51 (2H, d, J=8Hz), 6.55 (4H, s), 6.80 (2H, d, J=4Hz), 7.0-7.4 (3H, m), 7.6-7.7 (3H, m)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18648-66-3, its application will become more common.
Reference:
Patent; IDEMITSU KOSAN CO., LTD.; EP1695952; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary