2-Bromopropane → 4-Isopropoxy-2-methyl-1-nitrobenzene

HRID 1017589Notes

Reaction equation

HRID 1017589 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenol

Product 1

HCID 184035344-Isopropoxy-2-methyl-1-nitrobenzeneYield 58.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-methyl-4-nitrophenol (4.59 g, 0.03 mol) and 2-bromopropane (4.06 g, 0.033 mol) was refluxed with potassium carbonate (10 g) in acetone (200 mL) for 5 hours. After cooling, the reaction mixture was filtered through celite and the residue was purified by flash column (9/1 of Hexane/EtOAc) to afford 3.42 g of 4-isopropoxy-2-methyl-1-nitrobenzene (58.5%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe residue was purified by flash column (9/1 of Hexane/EtOAc)

Sources & evidence

ORD record
ord-e45cf79fc02248d696ed2a1af0cf373d
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

Loading…