These common heterocyclic compound, 5473-01-8, name is 2-Bromo-6-methoxyaniline, its 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. name: 2-Bromo-6-methoxyaniline
To a cooled (in an ice bath) suspension of 6-bromo-2-anisidine (63.52 g, 0.314 mol) in concentrated hydrochloric acid (130 ml) was added dropwise a solution of sodium nitrite (22 g, 0.32 mol) in water (100 ml) while the temperature was kept below 5 °C. After stirring for a further 30 min at 4 °C the red solution of the diazo compound was filtered and to the filtrate the chilled solution of tin(II) chloride dihydrate (175 g, 0.78 mol) in concentrated hydrochloric acid (200 ml) was added dropwise while occasionally adding water (all together ca. 500 ml water were added), while hydrazine hexachlorostannane precipitated. The reaction mixture was allowed to warm to room temperature and stirred for 3 h, after which the product was filtered off, and washed with saturated brine once. The solid was dissolved by the careful addition to a chilled aqueous solution of 25percent sodium hydroxide (200 ml) containing ca. 40 g of potassium tartrate. The product was extracted with dichloromethane (4 .x. 50 ml). The combined organic layers were washed with 2 M NaOH and water, dried over MgSO4 and evaporated to give 59.4 g (87percent) of desired product as a tan solid. Mass spectrum, m/z (I rel., percent): 219 (9), 218 (95), 217(10), 216 (100), 203 (64), 201(74), 200 (83), 198 (80), 186 (39).
The synthetic route of 2-Bromo-6-methoxyaniline has been constantly updated, and we look forward to future research findings.