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ChemicalBook CAS DataBase List 2-Fluorophenylacetone
2836-82-0

2-Fluorophenylacetone synthesis

11synthesis methods
1-(2-FLUOROPHENYL)-2-NITROPROPENE

829-40-3

2-Fluorophenylacetone

2836-82-0

General procedure for the synthesis of 2-o-fluoropropiophenone from (2-fluorophenyl)-2-nitropropene: a suspension of 1-fluoro-2-(2-nitroprop-1-en-1-yl)benzene (2054547) (160 g, 0.88 mol), powdered iron (320 g, 5.71 mol) and ferric(III) chloride (3.2 g, 19.6 mmol) in 640 ml of water, was heated to 80°C with stirring and 37% hydrochloric acid (320 ml) was added slowly over a period of 20 min. Subsequently, the reaction mixture was heated to reflux state kept for 1 hour and then cooled to room temperature. Ethyl acetate (1 L) was added and the mixture was filtered through a diatomaceous earth pad to separate the organic and aqueous layers. The organic layer was dried and concentrated and the crude product obtained was purified by distillation under reduced pressure to give 1-(2-fluorophenyl)propan-2-one (2054549) (90 g, 67% yield) with Rf = 0.40 (ethyl acetate:heptane = 1:4) and a boiling point of 70 °C (1 mmHg).

-

Yield:2836-82-0 96%

Reaction Conditions:

with lithium bromide in tetrahydrofuran;diethyl ether; for 1 h;Heating;

References:

Werbel;Cook;Elslager;Hung;Johnson;Kesten;McNamara;Ortwine;Worth [Journal of Medicinal Chemistry,1986,vol. 29,# 6,p. 924 - 939]

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