Related Products of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, 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.
(RS)-1-(3-Bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol Magnesium turnings (981 mg) and a crystal of iodine were suspended in tetrahydrofuran (10 mL) at room temperature. To this was added ~5 mL of a solution of 4-bromo-2-methylanisole (7.1 g) in tetrahydrofuran (100 mL). The mixture was then heated at reflux until initiation (colour change from brown to colourless ~15-30 min) after which time the heat was removed. The remaining 4-bromo-2-methylanisole solution was added dropwise to maintain a gentle reflux and the resultant mixture was then heated at reflux for 2 h. Upon cooling to room temperature, a solution of 1-(3-bromo-2-fluorophenyl)-ethanone (7.3 g) in tetrahydrofuran (100 mL) was added dropwise, again maintaining a gentle reflux and this was then heated at reflux for 2 h before being allowed to cool to room temperature. The mixture was then poured onto ice-water (400 mL) and the solvent removed by evaporation. The product was extracted with ethyl acetate (3*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield a yellow oil. Purification by flash chromatography on silica (20:1-5:1 hexanes/ethyl acetate) yielded (R,S)-1-(3-bromo-2-fluorophenyl)-1-(4-methoxy-3-methylphenyl)ethanol as a yellow oil (6.37 g, 56%). 1H NMR (CDCl3): 1.94 (3H, s, ArCH3), 2.17 (3H, s, ArCH3), 3.80 (3H, s, ArOCH3), 6.75 (1H, d, Ar), 7.00-7.16 (3H, m, Ar), 7.47 (1H, t, Ar), 7.63 (1H, t, Ar).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methoxy-2-methylbenzene, its application will become more common.
Reference:
Patent; Andreini, Matteo; Gabellieri, Emanuele; Guba, Wolfgang; Marconi, Guido; Narquizian, Robert; Power, Eoin; Travagli, Massimiliano; Woltering, Thomas; Wostl, Wolfgang; US2009/209529; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem