Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. 2674-34-2
K2CO3 (1.13g, 8.19mmol), boronate ester 17 (800mg, 1.78mmol), and dibromoarene 11 (176mg, 0.593mmol) in toluene (20mL), EtOH (4mL) and H2O (2mL) was sparged with Ar for 1h. Pd(PPh3)4 (73mg, 0.063mmol) was added, the mixture was sparged with Ar for an additional 20min, and then heated 90C for 16h. The reaction mixture was cooled to rt and diluted with 50mL of H2O. The reaction mixture was extracted with Et2O (3¡Á50mL). The combined organics were washed with 150mL of brine, dried with Na2SO4, and the solvents were removed under vacuum. The product was isolated via column chromatography as a white solid (433mg, 99%), mp 248-250C. 1H NMR (CDCl3): delta 8.09 (d, J=1.8Hz, 2H), 7.80 (dd, J=8.0, 1.8Hz, 2H), 7.53 (d, J=8.0Hz, 2H), 7.49 (s, 6H), 6.91 (s, 2H), 3.76 (s, 12H), 1.41 (s, 36H). 13C NMR (CDCl3): delta 169.0, 151.3, 150.3, 141.6, 136.8, 132.2, 131.6, 130.3, 129.9, 128.4, 121.8, 121.7, 112.8, 56.0, 51.8, 35.0, 31.5. FTIR (cm-1): 1720.79. UV-vis (CH2Cl2) lowest E abs lambdamax [nm] ( [M-1cm-1]): 337 (22,801). Em. (CH2Cl2) lambdamax [nm]: 424. Anal. Calcd for C52H62O6: C, 79.76; H, 7.98. Found: C, 77.41; H, 8.18.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2674-34-2, its application will become more common.
Reference:
Article; Dressler, Justin J.; Miller, Sarah A.; Meeuwsen, Brian T.; Riel, Asia Marie S.; Dahl, Bart J.; Tetrahedron; vol. 71; 2; (2015); p. 283 – 292;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem