Application of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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.
The Pd-catalyzed cross-coupling reaction of 5-Bromo-l,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl~l,3-dimethoxybenzene 1 in excellent yield; Example 20 Synthesis of 5-AUyl-l,3-dimethoxybenzene5-Bromo-l,3-dimethoxybenzene (2.13 g, 9.8 mralphaol), CsF (2.88 g, 19.0 mmol), and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were weighed into a flame-dried Schlenk flask and put under a flow of argon. THF (80 mL) was added to the flask via syringe, and the resulting suspension was stirred for 30 min at room temperature. AHyI boronic acid pinacol ester (2.96 g, 17.6 mmol) in THF (40 ml) was added and the resulting mixture was heated to reflux for 30 h. Another portion of CsF (2.88 g, 19.0 mmol) and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were added and the reaction was continued to reflux for 24 h. The reaction mixture was diluted with petroleum ether (100 ml) followed by H2O (100 ml). The layers were separated and the aqueous layer was extracted with petroleum ether (2 x 80 ml). The combined organic layers were washed with H2O (100 ml), and brine (100 ml). The solution was dried over MgSO4 and evaporated to dryness. The crude product was purified by column chromatography (silica, eluent: hexanes/benzene = 3:2) to give 1.60 g (92%) of 5-Allyl-l,3- dimethoxybenzene. 1H NMR (CDCl3): delta 3.33 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 3.77 (s, 6H, OCHi), 5.02-5.11 (m, 2H5. CH2CH=CH2), 5.89-5.99 (m, 1Eta, CH2CH=CH2), 6.33-6.38 (m, 3H).
The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; RUTERGS UNIVERSITY; WO2007/8847; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem