589-10-6, name is (2-Bromoethoxy)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H9BrO
Upon stirring a solution of p-anisoyl chloride (8.53 g, 50 mmol) and beta-bromophenetole (10.05 g, 50 mmol) in 20 mL of anhydrous nitrobenzene at 5 C. under a nitrogen atmosphere, 7.33 g (55 mmol) of anhydrous aluminum chloride was added portionwise. The resulting mixture was stirred at room temperature for 1 hour then at a reduced pressure for 5 minutes to remove the HCl gas produced during the reaction. Stirring was continued at room temperature under the nitrogen atmosphere for another hour. Nitrobenzene was removed at 45 C./0.4 mmHg and the solids deposited were dissolved in 60 mL of chloroform. Upon stirring the solution in an ice bath, 25 mL of 2M HCl was added portionwise. The organic layer was separated and washed with 20 mL of saturated sodium hydrogencarbonate aqueous solution, dried over solid NaHCO3, and filtered through a filter paper. Solvent was removed from the filtrate using a rotary evaporator and the crude product was purified by silica gel column chromatography (particle size 32-63) in CHCl3. The product with Rf=0.26 was collected and recrystallized from chloroform/hexane to give 14.44 g (43 mmol, 86% yield) of white flakes. m.p. 112.2-113.3 C. E.A. C16H15BrO3, calculated C 57.32, H 4.52, Br 23.83; found C 57.40, H 4.55, Br 23.76. 1H-NMR (DMSO-d6) delta 3.86 (m, 5H, -OCH3, -OCH2CH2Br), 4.44 (t, 2H, J=5.40, 5.04 Hz, -OCH2CH2Br), 7.08 (d, 2H, J=8.64 Hz, aromatic H’s), 7.11 (d, 2H, J=8.64 Hz, aromatic H’s), 7.71 (d, 2H, J=2.52 Hz, aromatic H’s), 7.73 (d, 2H, J=2.52 Hz, aromatic H’s). 13C-NMR (DMSO-d6) 31.17, 55.51, 67.97, 113.75, 114.33, 129.88, 130.44, 131.84, 161.11, 162.54, 193.12.
The synthetic route of 589-10-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Mills, Randell L.; Wu, Guo-Zhang; US2005/80260; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem