Reference of 51554-93-9,Some common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, molecular formula is C14H21Br, 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.
To the solution of 1 -bromo-4-octylbenzene (3.733 g; 12.48 mmol;) in dry THF (20.0 cm3) at -78 C was added n-BuLi (5.0 cm3; 12.5 mmol). The mixture was stirred at -78 C for 2 hours to yield a pale-yellow clear solution. The solid of diethyl 2,5-di(thieno[3,2-b]thiophen-2-yl)terephthatate (3) (1.30 g; 2.60 mmol) was added in one portion and the mixture (a yellow suspension) was stirred at -78 C for 20 minutes. The cooling bath was removed and the mixture was stirred at 22 C for 50 hours to yield a deep yellow clear solution. Saturated ammonium chloride solution (50 cm3) was added and the mixture was stirred for 15 minutes. The orange oil was taken into diethyl ether (2 x 50 cm3). The solvent was concentrated till a yellow solid started crashing out. Methanol (50 cm3) was added to the residue and the precipitate was collected by suction filtration and washed with methanol.The solid was dissolved in dry DCM (50 cm3) andBF3 etherate (1.0 cm3; 8.10 mmol) was added. The blue clear solution was stirred at 22 C for 1 hour followed by the addition of methanol (150 cm3). The yellow precipitate was suction filtered off and washed with methanol. The solid was further purified by flash column chromatography on silica (9:1 petroleum ether 40- 60-chloroform) to yield the productas a bright-yellow solid (1.06 g, 36%). *H-NMR (CDCI3, 300 MHz): delta= 0.86 (t, J = 6.7 Hz, 6H), 1.25 (m, 20H), 1.58 (m, 4H), 2.54 (t, J = 7.8 Hz, 4H), 7.07 (d, J = 8.3 Hz, 4H), 7.18 (d, J = 8.3 Hz, 4H), 7.25 (d, J = 5.2 Hz, 1H), 7.27 (d, J = 7.2 Hz, 1H), 7.50 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-octylbenzene, its application will become more common.
Reference:
Patent; MERCK PATENT GMBH; WANG, Changsheng; TIERNEY, Steven; D’LAVARI, Mansoor; NANSON, Lana; WO2013/10614; (2013); A2;,
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bromide – Wiktionary