1-Bromo-5-methoxynaphthalene synthesis
- Product Name:1-Bromo-5-methoxynaphthalene
- CAS Number:74924-95-1
- Molecular formula:C11H9BrO
- Molecular Weight:237.09
52927-23-8
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Yield:74924-95-1 90%
Reaction Conditions:
with potassium carbonate;tetrabutylammomium bromide in acetonitrile; for 16 h;
Steps:
1
Preparation of Final Title Compound. [0098] Purified 5-bromo-1-naphthol (3.22 g, 14.4 mmol), was dissolved in CH3CN (50 mL), giving a clear and nearly colorless solution. Dimethylsulfate (2.72 g, 21.6 mmol, 1.5 equiv), K2CO3 (3.0 g, 21.6 mmol), and tetrabutylammonium bromide (TBAB, 20 mg) as phase transfer catalyst were added, and the resulting mixture was stirred for 16 h. HPLC revealed no detectable starting material, when H2O (50 mL) was added. The inorganic salt promptly dissolved, followed immediately by crystallization of the product. Following filtration, an H2O wash (50 mL) of the cake, and drying in vacuo at 50° C., provided the final title compound as a light tan crystalline solid (3.07 g, 90.0%): mp 68.5-69.5° C. Satisfactory elemental analysis was obtained when block dried at 60° C. HPLC of 99.6%.
References:
US2004/6229,2004,A1 Location in patent:Page/Page column 14
3698-28-0
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68449-30-9
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529-34-0
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