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With dihydrogen peroxide In ethanol at 80℃; for 0.5 h;
Hydrogen peroxide (0.55 ml_, 5.38 mmol) was added to (5-chloro-2- methoxyphenyl)boronic acid (5 g, 26.82 mmol) in EtOH (100 ml_). The resulting solution was stirred at 80 C for 30 minutes, then cooled to room temperature naturally. The solvent was removed under reduced pressure. The residue was dissolved in DCM (200 mL), then washed with saturated brine (100 mL x2), The organic layer was dried over Na2S04, filtered and evaporated to afford 5-chloro-2-methoxyphenol (4.19 g, 99 percent)
95%
Stage #1: at 20℃; for 0.333333 h; Stage #2: With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In acetone at 0 - 20℃; for 24 h; Stage #3: With hydrogenchloride; sodium sulfite In ethyl acetate; acetone
To a solution of (5-chloro-2-methoxyphenyl)boronic acid (5.Og, 26.82mmol) in water (2OmL) was added sodium hydroxide pellets (1.6g, 40.23mmol) at rt. The reaction mixture was stirred for 20 min and then sodium hydrogen carbonate solution (2OmL) was added, followed by acetone (5OmL) and EDTA (0.8g, 2.68mmol). The mixture was cooled to 0 °C and Oxone.(R). (18.Og, 29.51 mmol) was added. The mixture was warmed to rt over 24h and sodium sulfite (1.2Og) was added followed by concentrated hydrochloric acid (15mL) and EtOAc (3OmL). The phases were separated and the aqueous phase was extracted with EtOAc (3OmL). The organic solutions were combined, dried over magnesium sulfate and the solvent was removed in vacuoto afford the desired compound, 4.Og (95percent). 1H NMR (400 MHz, CDCI3) δ 3.90 (3H, s), 5.60 (1 H, s), 6.80 (1 H, d), 6.90 (1H, d), 6.95 (1 H, s).
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 23h;Heating / reflux;
Example 12a) Preparation of 4-chloro-1-methoxy-2-(2-methoxy-benzyl)-nitrobenzene<strong>[3913-23-3]2-Methoxy-5-nitrobenzyl bromide</strong> (3.23 g, 13.11 mmol) and 5-chloro-2-methoxyphenyl boronic acid (2.43 g, 13.11 mmol) are dissolved in THF (180 mL) and treated with Pd(PPh3)4 (0.72 g, 0.625 mmol). The reaction mixture is stirred under an atmosphere of argon in the dark and a solution of Na2CO3 (3.5 g, 33 mmol) in water (10 mL) is added and the reaction is heated to reflux for 23 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is evaporated and the residue purified by flash chromatography over EPO <DP n="27"/>silica gel eluting with 25:75 EtOAc:isohexane to afford 4-chloro-1-methoxy-2-(2-methoxy- benzyl)-nitrobenzene; MH+ = 308.
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