Ethanol → 5-Bromo-N-ethyl-2-nitroaniline

HRID 1430161Notes

Reaction equation

HRID 1430161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C[NH2:13].[CH3:14][CH2:15]O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:13][CH2:15][CH3:14])[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 249029765-Bromo-N-ethyl-2-nitroaniline

Conditions

Temperature
85 °C

Procedure

A mixture of 4-bromo-2-fluoro-nitrobenzene (6 g, 27.3 mmol), methylamine (2M in MeOH, 34.1 mL, 68.2 mmol, 2.5 eq) and EtOH (80 mL) is stirred for 15 h at 85° C., allowed to cool and concentrated. The residue purified by trituration to afford 6 g of the title compound as an yellow solid: tR=5.13 min (System 1).

Workup

  1. temperatureto cool
  2. concentrationconcentrated
  3. customThe residue purified by trituration

Sources & evidence

ORD record
ord-96f687ae09d64f09a56889eb585bfc53
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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