Reference of 18869-30-2,Some common heterocyclic compound, 18869-30-2, name is (E)-1,2-Bis(4-bromophenyl)ethene, molecular formula is C14H10Br2, 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.
[0106] (3) N,N,N?,N?-tetra(2-naphthyl)-4,4?-diaminostilbene was prepared. The reaction scheme is shown in the following: [0107] Into a 50 ml two-necked flask, 420 mg (1.56 mmol, 2.1 eq) of di-2-naphthylamine obtained in (2), 250 mg (0.741 mmol) of 4,4-dibromostilbene, 3.4 mg (0.0148 mmol, 2.0% by mole) of palladium acetate and 157 mg (1.63 mmol, 2.2 eq) of sodium t-butoxide were placed. A rubber cap was placed at the side opening of the flask. A coiled tube condenser for refluxing was attached to the central opening of the flask and a three-way stopcock attached with a balloon containing the argon gas was attached to the top of the coiled tube condenser. The atmosphere in the system was purged with the argon gas in the balloon 3 times using a vacuum pump. [0108] To the above system, 10 ml of dehydrated toluene and 13.4 ?l (0.0296 mmol, 4.0% by mole) of a 2.22 moles/liter toluene solution of tris-t-butylphosphine were added using a syringe through a rubber septum. Then, the flask was set into an oil bath and the temperature was raised slowly to 115 C. while the solution was stirred. Brownish white precipitates were formed in the reaction solution after 30 minutes. After heating at 115 C. for 6 hours under stirring, the flask was removed from the oil bath and left standing for one night. [0109] The formed precipitates were completely dissolved in 500 ml of dichloromethane. After the resultant fluid was transferred to a separation funnel and washed with 100 ml of a saturated aqueous solution of sodium chloride, the organic layer (yellow) was dried with anhydrous potassium carbonate. After filtration, the organic solvent was removed by distillation and 150 ml of toluene and 50 ml of ethanol were added to the obtained residue. After a drying tube was attached to the flask, the precipitates were dissolved to some degree by heating at 80 C. and the resultant mixture was slowly cooled to the room temperature. The crystals of the ivory color in the system were separated by filtration using a Kiriyama funnel. After the crystals were washed with small amounts of toluene and ethanol and dried at 60 C. for 3 hours in a vacuum drying chamber, 428 mg (0.600 mmol) of N,N,N?,N?-tetra(2-naphthyl)-4,4?-diaminostilbene was obtained at a yield of 81%. [0110] The results of the measurements of NMR and FD-MASS on the obtained N,N,N?,N?-tetra(2-naphthyl)-4,4?-diaminostilbene were as follows: [0111] NMR: ?90 MHz 6.9 to 7.9 (38H, m) [0112] FD-MASS: 714
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-1,2-Bis(4-bromophenyl)ethene, its application will become more common.
Reference:
Patent; Iwakuma, Toshihiro; Moriwaki, Fumio; US2004/82813; (2004); A1;,
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