1,2-Dibromoethane → 2-(4-Amino-3-nitrophenoxy)ethyl bromide

HRID 415060Notes

Reaction equation

HRID 415060 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Br:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Br:12][CH2:13][CH2:14][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 154854442-(4-Amino-3-nitrophenoxy)ethyl bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A round-bottom flask was charged with 4-amino-3-nitrophenol (15.4 g, 0.1 mol, commercially available from Aldrich), acetone (600 mL), 1,2-dibromoethane (34.5 mL, 0.4 mol) and cesium carbonate (39 g, 0.12 mol). The mixture was refluxed 15 hours with stirring. The mixture was filtered to remove the salt, the filtrate was concentrated. Purification by the silica gel chromatography gave 4-(2-bromoethoxy)-2-nitroaniline (6.5 g). 1H-NMR (400 MHz, CDCl3): δ 7.57 (d, 1H), 7.12 (dd, 1H), 6.80 (d, 1H), 5.95 (s, br, 2H), 4.27 (t, 2H), 3.64 (t, 3H). MS (EI): 262 (MH+).

Workup

  1. temperatureThe mixture was refluxed 15 hours
  2. filtrationThe mixture was filtered
  3. customto remove the salt
  4. concentrationthe filtrate was concentrated
  5. customPurification by the silica gel chromatography

Sources & evidence

ORD record
ord-187bf8bf9b794d989d6c258914eb91af
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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