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

Appearance

Off-white to light yellow Solid

Safety Information

HS Code 

2914500090

5-Bromo-2-methoxyacetophenone Usage And Synthesis

Preparation

Preparation by reaction of methyl iodide with 5-bromo-2-hydroxyacetophenone in the presence of potassium carbonate in refluxing acetone for 3 h (86%).

Synthesis

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

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