Aniline → 4-Bromo-2-nitro-N-phenylaniline

HRID 2402660Notes

Reaction equation

HRID 2402660 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 124596324-Bromo-2-nitro-N-phenylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-bromo-4-fluoro-3-nitrobenzene (2270 mg, 10.01 mmol), aniline (3 ml) and DMF (20 ml) was heated at 100° C. under an atmosphere of Nitrogen for 7 h. The mixture was then concentrated in vacuo, and the residue triturated with heptane (30 ml) to give the desired product. 18 NMR (400 MHz, CDCl3) δ=7.11 (d, 1H, J=9.2 Hz), 7.25-7.29 (m, 3H), 7.40-7.45 (m, 3H), 8.35 (d, 1H, J=2.4 Hz) and 9.45 (brs, 1H).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue triturated with heptane (30 ml)

Sources & evidence

ORD record
ord-389254f51f5d40cbbf2b530c5c525cab
Source dataset
uspto-grants-2014_08
Patent number
US08796455B2

Reaction notes

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