Synthetic Route of 588-96-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 588-96-5 name is p-Bromophenetole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
General procedure: A 15 mL screw cap test tube was charged with Cu(OAc)2*H2O (20 mg, 0.1 mmol, 2 mol %), L4 (78 mg, 0.4 mmol, 8 mol %), hexane-2,5-dione (46 mg, 0.4 mmol, 8 mol %), KOH (650 mg, 10 mmol, 200 mol %), adipic acid (219 mg, 1.5 mmol, 30 mol %), NaOAc (246 mg, 3 mmol, 60 mol %), CTAB (182 mg, 0.5 mmol, 10 mol %), H2O (0.5 mL), aryl bromide (5 mmol) and amine (6.5 mmol, 130 mol %). Argon (flow rate 5-7 mL/min) was bubbled through the resulting mixture for 5 min. The reaction mixture was stirred in a closed test tube at 100C for 3-4 h until complete consumption of starting material as monitored by TLC (eluent-hexane), then cooled to room temperature and diluted with EtOAc (30 mL). The EtOAc solution was purified by flash-chromatography, washed with water (310 mL), and dried with anhydrous Na2SO4. Then EtOAc was evaporated under reduced pressure and the residue was recrystallized from hexane (substances 1-4) or aq EtOH (substances 5-9). In a case of the substances 5, 7-9 the residue was dissolved in diethyl ether. Aq HCl (37%) was added dropwise to the resulting solution until pH 3-4. The formed precipitate was filtered, washed with diethyl ether (10 mL) and dried at 50 C.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, p-Bromophenetole, and friends who are interested can also refer to it.
Reference:
Article; Kurandina; Eliseenkov; Khaibulova; Petrov; Boyarskiy; Tetrahedron; vol. 71; 41; (2015); p. 7931 – 7937;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem