2'-FLUORO-6'-METHOXYACETOPHENONE Chemical Properties

Boiling point:

217℃

Density 

1.127

refractive index 

1.508

Flash point:

83℃

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

color 

Clear, lemon/pale amber

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2914790090

2'-FLUORO-6'-METHOXYACETOPHENONE Usage And Synthesis

Uses

1-(2-Fluoro-6-methoxyphenyl)ethanone is a useful synthetic intermediate. It is used to prepare spiro[2H-1-benzopyran-2,4''-piperidine] derivatives as glycine transport inhibitors.

Synthesis

General procedure for the synthesis of 2-fluoro-6-methoxyacetophenone from 1-(2-fluoro-6-methoxyphenyl)ethan-1-ol: Pyridinium dichromate (44 g, 0.116 mol) was added to a solution of N,N-dimethylformamide (130 mL) of 1-(2-fluoro-6-methoxyphenyl)ethan-1-ol (13.1 g, 0.077 mol). stirred at room temperature for 12 hours. Upon completion of the reaction, water (300 mL) was added to the reaction mixture, diluted with ethyl acetate and filtered through diatomaceous earth. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-fluoro-6-methoxyacetophenone as a brown liquid (9.2 g, 70% yield).1H-NMR (δ ppm, CDCl3, 400 MHz): 7.73 (dd, J = 15.1, 8.4 Hz, 1H), 6.73 (m, 2H), 3.85 (s, 3H), 2.53 (s, 3H), 3.85 (s, 3H), 3.85 (s, 3H), 3.85 (s, 3H). 3H), 2.53 (s, 3H).

References

[1] Journal of the American Chemical Society, 2016, vol. 138, # 5, p. 1486 - 1489
[2] Patent: US2012/289496, 2012, A1. Location in patent: Page/Page column 100
[3] Patent: WO2012/151525, 2012, A1. Location in patent: Page/Page column 101

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