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

HRID 1068605Notes

Reaction equation

HRID 1068605 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 (CH 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-4d74f826a7da43e5ab2804fc6036a716
Source dataset
uspto-grants-2001_06
Patent number
US06251903B1

Reaction notes

Loading…