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

HRID 1600717Notes

Reaction equation

HRID 1600717 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-0804e493577146e2ab44bc7ddcca7141
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

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