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5-Bromo-2-methoxyacetophenone

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5-Bromo-2-methoxyacetophenone Basic information
Product Name:5-Bromo-2-methoxyacetophenone
Synonyms:JR-8526, 1-(5-Bromo-2-methoxyphenyl)ethanone, 97%;Ethanone, 1-(5-bromo-2-methoxyphenyl)-;5'-Bromo-2'-methoxyacetophenone;5-BROMO-2-METHOXYACETOPHENONE;1-(5-Bromo-2-methoxyphenyl)ethan-1-one
CAS:16740-73-1
MF:C9H9BrO2
MW:229.07
EINECS:604-604-1
Product Categories:
Mol File:16740-73-1.mol
5-Bromo-2-methoxyacetophenone Structure
5-Bromo-2-methoxyacetophenone Chemical Properties
Melting point 39 °C
Boiling point 165 °C
density 1.421±0.06 g/cm3(Predicted)
storage temp. Store at room temperature
AppearanceOff-white to light yellow Solid
Safety Information
HS Code 2914500090
MSDS Information
5-Bromo-2-methoxyacetophenone Usage And Synthesis
PreparationPreparation by reaction of methyl iodide with 5-bromo-2-hydroxyacetophenone in the presence of potassium carbonate in refluxing acetone for 3 h (86%).
Synthesis
2'-Methoxyacetophenone

579-74-8

5-Bromo-2-methoxyacetophenone

16740-73-1

General procedure for the synthesis of 1-(5-bromo-2-methoxyphenyl)-acetophenone from 2'-methoxyacetophenone: N-bromosuccinimide (NBS, 1.5 eq., 0.3 mmol), catalyst (10 mol%, 0.02 mmol), and acetonitrile (CH3CN, 1.0 mL) were added to the reaction tube, followed by 2'-methoxyacetophenone (0.2 mmol). The reaction mixture was stirred for 12 h at room temperature protected from light. After completion of the reaction, the reaction was quenched with saturated sodium thiosulfate (Na2S2O3) aqueous solution (2 mL). The reaction mixture was extracted with ethyl acetate (3.5 mL). The organic phases were combined, washed with brine (10 mL), dried over anhydrous sodium sulfate (Na2SO4), and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure and the residue was purified by rapid chromatography on a silica gel column using petroleum ether/dichloromethane (5:1) as eluent to afford the target product 1-(5-bromo-2-methoxyphenyl)-ethanone.

References[1] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
[2] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4707 - 4710
[3] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 312-313
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1423 - 1428
[5] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504
5-Bromo-2-methoxyacetophenone Preparation Products And Raw materials
Raw materials2'-Methoxyacetophenone-->5-Bromo-2-hydroxyacetophenone-->Iodomethane-->Acetonitrile-->iodine-->N-Bromosuccinimide
Preparation Products5-Bromo-2-hydroxyacetophenone-->Benzenemethanol, 2-methoxy-α,5-dimethyl-, (αR)-
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