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

HRID 972353Notes

Reaction equation

HRID 972353 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1I.Br[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19]>>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

3

Reactant 2

HCID 770041,4-Dibromo-2-nitrobenzeneHCID 968642,4-Dichloro-1-iodobenzene

Product 1

HCID 21406766HCID 21406766, compound

Procedure

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.

Sources & evidence

ORD record
ord-fb17acd1b5504fb3977a541999bd5604
Source dataset
uspto-grants-1977_10
Patent number
US04052514

Reaction notes

Loading…