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

HRID 1781009Notes

Reaction equation

HRID 1781009 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): δ7.863 (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-20edf21ec70840f0a6212c3319d100fd
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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