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

HRID 415111Notes

Reaction equation

HRID 415111 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].C(=O)([O-])[O-].[Cs+].[Cs+].[Br:18][CH2:19][CH2:20]CBr>CC(C)=O>[Br:18][CH2:19][CH2:20][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 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 37588824-Amino-3-Nitrophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 500 mL flask was charged with 4-amino-3-nitrophenol (15.4 g, 100 mmol, commercially available from Aldrich). Acetone (300 mL), cesium carbonate (39.09 g, 120 mmol) and 1,3-dibromopropane (40.84 mL, 400 mmol) were added to the flask and stirred at refluxed temperature. The reaction was monitored by LCMS. After 6 hours, the reaction mixture was cooled to room temperature, filtered and washed with acetone. The organic layer was removed on a rotary evaporator under reduced pressure and the resulting material was purified by silica column chromatography using 40% hexane in dichloromethane as eluant. 20 g of 4-(2-bromoethoxy)-2-nitroaniline was isolated which was used in the next step without any further purification. MS (EI): 275 (MH+).

Workup

  1. temperatureat refluxed temperature
  2. filtrationfiltered
  3. washwashed with acetone
  4. customThe organic layer was removed on a rotary evaporator under reduced pressure
  5. customthe resulting material was purified by silica column chromatography

Sources & evidence

ORD record
ord-0cea06db1f564126b1904534511c36cc
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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