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CAS No. : | 14938-58-0 | MDL No. : | MFCD00099247 |
Formula : | C11H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CBEFAHWSHVJUKE-UHFFFAOYSA-N |
M.W : | 237.09 | Pubchem ID : | 2780087 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | (8-Bromonaphthalen-l- yl)methanol (0.24 g, 0.99 mmol) was dissolved in THF (5 mL) and cooled to 0 C. NaH (60% in mineral oil, 79 mg, 2.0 mmol) was added and the reaction was stirred for 30 minutes. Methyl iodide (0.093 mL, 1.5 mmol) was added, the solution was slowly warmed to room temperature, and the reaction was stirred for 16 hours. The reaction was diluted with EtO Ac and quenched with saturated aqueous NHCl. The organics were separated and the aqueous phase was extracted with EtO Ac. The organics were dried over MgS04, condensed, and purified by flash chromatography (RediSep Gold 12 g column, 0-10% EtO Ac/hexane) to afford l-bromo-8- (methoxymethyl)naphthalene (0.18 g, 71%). NMR (CDCb, 400 MHz): d 7.87-7.79 (m, 3H), 7.74 (d, J= 7.1 Hz, 1H), 7.46 (t, J= 7.7 Hz, 1H), 7.25 (t, J= 7.8 Hz, 1H), 5.33 (s, 2H), 3.52 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 mg | With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; | (8-Bromo-1-naphthyl)methanol 149 (210 mg, 1.0 equiv.), phenol 150 (130 mg, 1.3 equiv.), triphenylphosp1ne (465 mg, 2.0 equiv.), triethylamine (0.25 mE, 2.0 equiv.) weredissolved in 2 mE THF and cooled to 00 C. under nitrogen.Diisopropyl azodicarboxylate (0.34 mE, 2.0 equiv.) wasadded dropwise and the mixture was warmed to rt and stirredovernight. The mixture was concentrated and purified usingflash silica gel chromatography (12 g, 0-10% EtOAc in hexanes) to provide coupled product 100 mg. Conversion toboronic acid 151 was achievedby Method 1. [M-H]295.1mlz. Activity: D |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium tetrahydroborate; ethanol; at 0 - 20℃; | 8-Bromo-l-naphthaldehyde (0.24 g, 1.0 mmol) was suspended in ethanol (5 mL). After the mixture was cooled to 0 C, NaBHi (57 mg, 1.5 mmol) was added. The mixture was warmed to room temperature, diluted with EtO Ac, and quenched with saturated aqueous MHCl. The organics were separated and the aqueous phase was extracted with ethyl acetate. The combined organics were dried over MgS04 and condensed to afford (8-bromonaphthalen- l-yl)methanol (0.24 g, 99%). NMR (400 MHz, CDCb): d 7.89- 7.83 (m, 3H), 7.71 (d, J= 7.0 Hz, 1H), 7.48 (t, J= 7.6 Hz, 1H), 7.28 (t, J= 7.7 Hz, 1H), 5.47 (d, J = 7.0 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With toluene-4-sulfonic acid; In dichloromethane; water; at 25℃; for 2h; | To a solution of (8-bromo-l- naphthyl)methanol (2.1 g, 8.86 mmol, 1.0 eq ) in dichloromethane (42 mL) was added TsOTbThO (168 mg, 886 pmol, 0.1 eq) and DHP (1.49 g, 17.7 mmol, 1.62 mL, 2.0 eq). The mixture was stirred at 25 C for 2 hours, and the mixture was concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate 10/1 to 3/1) to give 2-[(8- bromo-l-naphthyl)methoxy]tetrahydropyran (2.7 g, 95% yield). Colourless oil; Rf = 0.80 (petroleum ether/ethyl acetate 10/1). |