Some common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, molecular formula is C15H23BrO, 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: 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene
Reference Example 3 Bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide Under argon atmosphere, a solution of magnesium (4.0 g, 0.95 equivalents) and a small amount of iodine in THF (50 mL) was stirred at room temperature for 1 hour. After 4-bromo-2,6-di-tert-butylanisole (52 g, 0.175 mol) synthesised in Reference Example 2 was added at 46C to 53C thereto, the mixture was stirred at 5C for 1 hour. Then, dimethyl phosphite (11.4 g, 0.52 equivalents) was added and the mixture was stirred at 5C for 1 hour. After water (50 mL) was added at 3C and toluene (50 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An organic layer was washed successively with water (20 mL), a 5% NaHCO3 aqueous solution (20 mL) and a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to obtain the title compound (11.6 g, pale yellowish white crystal). Yield 20.5%, mp. 166.1C. 1H-NMR (300 MHz, CDCl3, TMS) delta: 1.38 (s, 36H), 3.68 (s, 6H) 7.49 (s, 2H), 7.54 (s, 2H), 8.01 (d, 1H, J = 474.4 Hz).31P-NMR (121 MHz, CDCl3, 85%H3PO4) delta: 23.57 (dquint, J=474.1 Hz, 14.0 Hz). Elementary analysis for C30H47O3P Calculated value; C: 74.04, H: 9.73, P: 6.36 Found value; C: 74.13, H: 9.93, P: 6.20.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1516-96-7, its application will become more common.
Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1568701; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem