588-96-5, name is p-Bromophenetole, 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. Quality Control of p-Bromophenetole
Preparation Example 3 Synthesis of 1-bromo-3-(4-ethoxybenzyl)benzene; A 2.6 M n-butylithium hexane solution (5.8 mL) was added to a mixture of 4-bromophenetole (2.87 g, 0.0143 mol) and tetrahydrofuran (30 mL) at -78C. After the mixture was stirred for 0.5 hours, a tetrahydrofuran (15 mL) solution of 3-bromobenzaldehyde (2.65 g, 0.0143 mol) was added, and further stirred for 15 minutes to warm the reaction mixture to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=7:1 to 5:1) to obtain colorless oily (3-bromophenyl)(4-ethoxyphenyl)methanol (3.94 g, 90%). Then, Et3SiH (4.09 mL, 0.0256 mol) and BF3·Et2O (1.47 mL, 0.0116 mol) were added sequentially to a chloroform (22 mL) solution of (3-bromophenyl)(4-ethoxyphenyl)methanol (3.92 g, 0.0128 mol) at -60C. After stirred for one hour, the reaction solution was warmed to room temperature. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain a colorless oily title compound (2.84 g, 76%). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 3.88 (s, 2 H) 4.01 (q, J=7.0 Hz, 2 H) 6.83 (d, J=8.9 Hz, 2 H) 7.07 (d, J=8.9 Hz, 2 H) 7.09 – 7.18 (m, 2 H) 7.29 – 7.34 (m, 2 H).
The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); A1;,
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