2'-FLUORO-6'-HYDROXYACETOPHENONE Chemical Properties

Boiling point:

224.0±20.0 °C(Predicted)

Density 

1.25g/ml

refractive index 

1.534

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

liquid

pka

9.17±0.10(Predicted)

color 

Clear, faint lime

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2914500090

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

Preparation

Preparation by reaction of boron tribromide on 2-fluoro-6- methoxyacetophenone (I) in methylene chloride at ?65° to ?80° (56%). The precursor (I) was obtained by reaction of methyl magnesium iodide on 2-fluoro-6-methoxybenzonitrile in refluxing toluene (quantitative yield).

Synthesis

General procedure for the synthesis of 2-fluoro-6-hydroxyacetophenone from 2-fluoro-6-methoxyacetophenone: aluminum chloride (14.3 g, 0.107 mol) was added to an ice-cold solution of intermediate 3 (9.0 g, 53.5 mmol) in dichloromethane (70 mL), followed by slow warming of the reaction mixture to room temperature. After the reaction was carried out for 12 h, the reaction was quenched with aqueous 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed sequentially with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-fluoro-6-hydroxyacetophenone as a brown liquid (5.48 g, 66% yield). The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 400 MHz): δ 12.72 (s, 1H, OH), 7.40 (m, 1H, Ar-H), 6.78 (d, J = 8.5 Hz, 1H, Ar-H), 6.62 (dd, J = 11.3, 8.3 Hz, 1H, Ar-H), 2.69 (d, J = 7.2 Hz, 3H, CH3).

References

[1] Patent: WO2012/151525, 2012, A1. Location in patent: Page/Page column 101
[2] Patent: US2012/289496, 2012, A1. Location in patent: Page/Page column 100
[3] Patent: US5399584, 1995, A
[4] Patent: US2007/14733, 2007, A1. Location in patent: Sheet 14
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 619 - 622

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