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

HRID 439533

Reaction equation

HRID 439533 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]>>[Br:1][C:2]1[C:3]([Cl:9])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([Cl:8])[CH:7]=1

Participants

3

Reactant 2

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

Product 1

HCID 211900161-Bromo-2,5-dichloro-4-nitrobenzeneYield 95%

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). The yellowish precipitate was filtered, washed with water (10 mL) and dried under vacuum to give 1.14 g (95%) of pure title compound as a yellowish powder; m.p. 50°-53° C.; 1H NMR (CDCl3):7.863 (s, 1H), 8.030 (s, 1H).

Workup

  1. filtrationThe yellowish precipitate was filtered
  2. washwashed with water (10 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-14e076c21e2747bbb3549255e159bd5b
Source dataset
uspto-grants-1996_05
Patent number
US05514680

Linked notes

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