4-bromo-2-methoxybenzeneethanol synthesis
- Product Name:4-bromo-2-methoxybenzeneethanol
- CAS Number:1289626-24-9
- Molecular formula:C9H11BrO2
- Molecular Weight:231.09
1289626-21-6
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Yield:1289626-24-9 66.1%
Reaction Conditions:
Stage #1: 4-bromo-2-methoxy-1-vinyl-benzenewith 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran at 0 - 25;Inert atmosphere;
Stage #2: with dihydrogen peroxide;sodium hydroxide in tetrahydrofuran;methanol;water at 0 - 25; for 2 h;
Steps:
5
Preparation of 9:2-(4-Bromo-2-methoxy-phenyl MethanolTo a solution of compound 8 (37 g, 0.174 mol) in anhydrous THF (400 mL) was added dropwise 9-BBN (418 mL, 0.209 mol) at 0°C under N2. After the addition, the reaction mixture was stirred at room temperature overnight. TLC (petroleum ether/ethyl acetate 5/1 ) indicated the reaction was complete. The mixture was cooled to 0°C and methanol (300 mL) was added, followed by the addition of 2 M NaOH solution (35 g, in 440 mL of H20) and H2O2 (185 ml_, 30% in water). The reaction mixture was then stirred at room temperature for 2 h. The mixture was concentrated in vacuo and the residue was suspended in water (200 mL) and extracted with diethyl ether (300 ml_x3). The combined organic layers were washed with brine (200 mL), filtered and the filtrate was concentrated in vacuo to give crude product (32 g), which was purified via column chromatography on silica gel (petroleum ether/ethyl acetate from 20/1 to 4/1 ) to give compound 9 (26.5 g, 66.1%) as a white solid.
References:
WO2011/45703,2011,A2 Location in patent:Page/Page column 35-36
1026089-09-7
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43192-33-2
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