ChemicalBook CAS DataBase List 1-(BENZYLOXY)-4-BROMO-2-METHOXYBENZENE

1-(BENZYLOXY)-4-BROMO-2-METHOXYBENZENE synthesis

5synthesis methods

Product Name:1-(BENZYLOXY)-4-BROMO-2-METHOXYBENZENE
CAS Number:63057-72-7
Molecular formula:C14H13BrO2
Molecular Weight:293.16

7368-78-7

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63057-72-7

Step 1: Synthesis of 1-(benzyloxy)-4-bromo-2-methoxybenzene (2). Potassium carbonate (K2CO3, 30.5 g, 221 mmol) and benzyl bromide (18.9 g, 171 mmol) were added to a solution of N,N-dimethylformamide (DMF, 150 mL) containing 4-bromo-2-methoxyphenol (15 g, 73.8 mmol). The reaction mixture was stirred at 100 °C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of water and the organic layer was extracted with ethyl acetate (EtOAc). The organic phases were combined and concentrated. The crude product was purified by column chromatography to afford the target compound 2 (17.6 g, 86% yield).

7368-78-7 Synthesis

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Yield: 100%

Reaction Conditions:

with caesium carbonate in acetone for 4 h;Heating / reflux;

Steps:

35 1-Benzyloxy-4-bromo-2-methoxy-benzene
Preparation 35 1-Benzyloxy-4-bromo-2-methoxy-benzene A mixture of 4-bromo-2-methoxyphenol (5 g, 24.63 mmol), benzyl bromide (4.21 g, 24.63 mmol) and cesium carbonate (8 g, 24.63 mmol) in acetone (60 mL) were heated under reflux for 4 hours. The cooled reaction mixture was then evaporated under reduced pressure and the residue was partitioned between diethyl ether (200 mL) and water (80 mL). The aqueous phase was separated and re-extracted with diethyl ether (200 mL). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was azeotroped with dichloromethane to afford the title compound as white solid in 100% yield, 7.19 g. LRMS (ES⁺): m/z [M+Na]⁺ 317

References:

PFIZER INC. US2005/43300, 2005, A1 Location in patent:Page/Page column 39

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2316-64-5 Synthesis