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

HRID 1632100Notes

Reaction equation

HRID 1632100 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH2:12].C1C(=O)N([Br:20])C(=O)C1>CC#N>[Br:20][C:5]1[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[NH2:12]

Participants

4

Reactant 2

HCID 73372-Methoxy-4-nitroanilineHCID 67184N-bromobutanimide

Product 1

HCID 70991182-bromo-6-methoxy-4-nitroaniline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 2 L round bottom flask with a stir bar was added 2-methoxy-4-nitro-phenylamine (50.0 g, 297.4 mmol), CH3CN (1 L), and NBS (53.5 g, 297.4 mmol). The reaction was stirred at room temperature for 2 hours while protected from light. The reaction was concentrated and then 500 mL water was added. The product was extracted with ethyl acetate and concentrated. The solid which precipitated from the aqueous washes was combined with the solid which resulted from the organic concentration to give I-229 (59.6 g) which was used without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. addition500 mL water was added
  3. extractionThe product was extracted with ethyl acetate
  4. concentrationconcentrated
  5. customThe solid which precipitated from the aqueous washes
  6. customresulted from the organic concentration
  7. customto give I-229 (59.6 g) which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-10a06d6f09ee4993b91ac0c6fa87df09
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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