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

HRID 990192Notes

Reaction equation

HRID 990192 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].[Br:13]N1C(=O)CCC1=O.CCCCCC.C(OCC)(=O)C>C(#N)C>[Br:13][C:6]1[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=[C:3]([O:2][CH3:1])[C:4]=1[NH2:5]

Participants

6

Reactant 4

HCID 73372-Methoxy-4-nitroanilineHCID 8058HexaneHCID 8857Ethyl AcetateHCID 67184N-bromobutanimide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A clear yellow solution of 2-methoxy-4-nitroaniline (10 g, 15 59.5 mmol) in acetonitrile (300 mL) at room temperature was treated with N-bromosuccinimide (10.58 g, 59.5 mmol). The reaction was protected from light and stirred for 2 hours at room temperature. TLC (3:1 hexane:ethyl acetate) analysis showed starting material (Rf 0.14) replaced with a higher spot (Rf 0.23). The reaction was concentrated in vacuo, treated with carbon tetrachloride, filtered through celite and concentrated in vacuo to give 2-bromo-6-methoxy-4-nitroaniline as a yellow brown solid. 1H NMR (δ, CDCl3): 8.11 (1H, d, J=2.2 Hz), 7.63 (1H, d, J=2.2 Hz), 4.96 (2H, br s), 3.96 (3H, s); MS (m/z) 249, 247.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiontreated with carbon tetrachloride
  3. filtrationfiltered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04d11d4e1ac1401085e1e7063f01dd32
Source dataset
uspto-grants-2002_10
Patent number
US06458935B1

Reaction notes

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