Sulfuric Acid → HCID 14677653, compound

Participants

Reaction Steps

An 11.4 g sample of the product of Example 1 (33 mmol) was added portionwise with stirring to a mixture of 36.5 mmol of 40% nitrosylsulfuric acid and 9 mL of concentrated sulfuric acid. The rate of addition was such that the internal temperature was maintained below 45° C. After the addition was completed, stirring was maintained at room temperature for 1.5 hours when the mixture was poured into 75 mL of ice water and filtered. To the filtrate, a solution of 2.2 g of sodium tetrafluoroborate in 15 mL of water was slowly added. The resulting mixture was refrigerated overnight, filtered and the precipitate washed with 12 mL of ice water. The precipitated tetrafluoroborate salt was then stirred in a mixture of 70 mL of water and 25 mL of ethyl acetate while a solution of 11 g (66 mmol) of potassium iodide in 40 mL of water was added over a 20 minute period. The resulting mixture was extracted with three 50 mL portions of methylene chloride which were combined and in turn extracted with 25 mL of 5% sodium thiosulfate solution. The organic extract was concentrated in vacuo to a residual solid which was dissolved in ether and refrigerated overnight. Impurities (mainly bromo-dichlorofluorenone, m.p. 183°-184° C.) were removed by filtration and the filtrate crystallized by concentration to the product which was then recrystallized from ether to produce (3-bromo-5-chloro-2-iodophenyl)(2-chlorophenyl)-methanone having a m.p. of 86°-87° C.

Provenance & Evidence