Tin tetrachloride → HCID 57814503, compound

Participants

Reaction Conditions

Reaction Steps

Twenty-four grams of a mixture containing (2,3-dibromo-6-fluoro-4-nitro-phenyl)-acetonitrile was dissolved in ethanol (500 mL) and tin (II) chloride dihydrate (85 g) was added. The mixture was stirred and heated at 75° C. for 5 h. 10 g more tin chloride was added and the mixture was heated at reflux for 30 additional minutes. The solution was cooled and most of the ethanol was removed in vacuo. The reaction mixture was diluted to a volume of 600 mL with ethyl acetate and 100 mL water was added. With stirring, sodium bicarbonate (75 g) was slowly added. The ethyl acetate layer was separated and the aqueous layer extracted a second time with ethyl acetate. The combined organic extracts were dried and the solvent removed in vacuo to afford 22.8 g of crude product. The title compound (3.8 g) was obtained from the crude mixture by column chromatography (hexane-ethyl acetate; then hexane-methylene chloride mixtures).

Provenance & Evidence