Nitric Acid → 1-Bromo-2,5-dichloro-4-nitrobenzene

HRID 1857391Notes

Reaction equation

HRID 1857391 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[Cl:9].[N+:10]([O-])([OH:12])=[O:11]>>[Cl:9][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([Cl:8])=[CH:7][C:2]=1[Br:1]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 150332-Bromo-1,4-dichlorobenzene

Product 1

HCID 211900161-Bromo-2,5-dichloro-4-nitrobenzene

Procedure

A solution of 2-bromo-1,4-dichlorobenzene (1.000 g, 4.443 mmol, Aldrich, used as received) in fuming HNO3 (7.0 mL) was stirred at 50° C. for 1.5 h and poured into ice (80 g). Yellowish white solid was filtered, washed with water (10 mL), and dried under vacuum to obtain 1.14 g (95%) of pure (1H NMR) title compound as a yellowish white powder; m.p. 50-53° C. (lit m.p. 57-58° C.; Fox, D. L. and Turner, E. E., J. Chem. Soc. 1859 (1930)); 1H NMR (CDCl3): δ 7.863 (s, 1H), 8.030 (s, 1H). This material was used as such for the next reaction.

Workup

  1. filtrationYellowish white solid was filtered
  2. washwashed with water (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-2e55e4fd496e47b19d76dd6c748b25ea
Source dataset
uspto-grants-2000_11
Patent number
US06147075

Reaction notes

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