1,4-Dibromo-2-nitrobenzene → HCID 21535988, compound

HRID 1077090Notes

Reaction equation

HRID 1077090 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1I>>[NH2:9][C:3]1[CH:4]=[C:5]([Br:8])[CH:6]=[CH:7][C:2]=1[C:16]1[CH:15]=[CH:14][C:13]([F:12])=[CH:18][C:17]=1[F:19]

Participants

3

Reactant 2

HCID 770041,4-Dibromo-2-nitrobenzeneHCID 1375192,4-Difluoro-1-iodobenzene

Product 1

HCID 21535988HCID 21535988, compound

Procedure

2,5-Dibromo-1-nitrobenzene and 2,4-difluoro-1-iodobenzene were reacted under Ullmann conditions to give 4-bromo-2',4'-difluoro-2-nitrobiphenyl, b.p. 126°-136°C./0.2mm (m.p. 52°-53°C. after recrystallisation from methanol). This was reduced to give 2-amino-4-bromo-2',4'-difluorobiphenyl, b.p. 120°-124°C./0.5mm, which was subjected to a Schiemann reaction, using hydrofluoroboric acid to give the product, m.p. 67°-69°C., after distillation.

Workup

  1. customto give
  2. custom4-bromo-2',4'-difluoro-2-nitrobiphenyl, b.p. 126°-136°C./0.2mm (m.p. 52°-53°C. after recrystallisation from methanol)

Sources & evidence

ORD record
ord-30dd1913e8f6462abaefb017fd012ced
Source dataset
uspto-grants-1976_05
Patent number
US03959364

Reaction notes

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