1,4-Dibromo-2-nitrobenzene → HCID 21406766, compound

Participants

Reaction Steps

2,4-Dichloroiodobenzene and 2,5-dibromonitrobenzene were reacted under Ullmann conditions to give 4-bromo-2',4'-dichloro-2-nitrobiphenyl, m.p. 112°-115° C. This was reduced with stannous chloride to give 2-amino-4-bromo-2',4'-dichlorobiphenyl, b.p. 170°-175° C./0.2 mm. This was subjected to the Schiemann reaction using fluoroboric acid to give 4-bromo-2',4'-dichloro-2-fluorobiphenyl, m.p. 63°-65° C. This was reacted with cuprous cyanide in dimethyl formamide to give 2',4'-dichloro-4-cyano-2-fluorobiphenyl, m.p. 98°-103° C. which was then reacted with methylmagnesium iodide followed by hydrolysis with dilute hydrochloric acid to yield 4-acetyl-2',4'-dihloro-2-fluorobiphenyl, m.p. 65°-67° C.

Provenance & Evidence