2-Methoxy-4-nitroaniline → 2-bromo-6-methoxy-4-nitroaniline

HRID 583181Notes

Reaction equation

HRID 583181 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:6]=1[NH2:7]>CC(O)=O>[Br:1][C:8]1[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:5]([O:4][CH3:3])[C:6]=1[NH2:7]

Participants

4

Reactant 2

HCID 73372-Methoxy-4-nitroanilineHCID 24408Bromine

Product 1

HCID 70991182-bromo-6-methoxy-4-nitroanilineYield 34.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

47.64 g of bromine in 120 mL of AcOH was added dropwise to a solution of 47.64 g of 2-methoxy-4nitro-aniline in 240 ml of AcOH at 0° C. Upon addition a precipitate formed. Mixture was stirred for 30 minutes and then filtered. The precipitate was washed with satd. NaHSO3, water, and vaccum dried, giving 24 g of title compound as a bright yellow powder.

Workup

  1. additionUpon addition a precipitate
  2. customformed
  3. filtrationfiltered
  4. washThe precipitate was washed with satd
  5. dry with materialNaHSO3, water, and vaccum dried

Sources & evidence

ORD record
ord-aac5ba348d0241f1af98e28cccfbc310
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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