1,3-Dibromopropane → 4-(3-Bromopropoxy)-2-nitroaniline

HRID 415120Notes

Reaction equation

HRID 415120 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][CH2:21]Br>CC(C)=O>[Br:18][CH2:19][CH2:20][CH2:21][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 220406544-(3-Bromopropoxy)-2-nitroaniline

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 and was complete in 6 hours. The reaction mixture was cooled to room temperature, filtered and washed with excess acetone. The organic layer was removed on a rotary evaporator under reduced pressure and the resulting brown gelatin was purified by silica column chromatography using 40% hexane in dichloromethane as eluent. 20.0 g of 4-(3-bromopropoxy)-2-nitroaniline was obtained as a dark orange liquid which was used without any further purification. MS (EI: 276 (MH+).

Workup

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

Sources & evidence

ORD record
ord-bc8a8eac1f2e4c5c879c8f6efb8ba0a4
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

Loading…