2-Bromopropane → 4-Bromo-1-isopropoxy-2-nitrobenzene

HRID 646175Notes

Reaction equation

HRID 646175 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.Br[CH:13]([CH3:15])[CH3:14].[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]([CH3:15])[CH3:14])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 243644-Bromo-2-nitrophenolHCID 2855718-Crown-6

Product 1

HCID 222832414-Bromo-1-isopropoxy-2-nitrobenzeneYield 61.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-bromo-2-nitrophenol (2.17 g, 10 mmol), 2-bromopropane (2.44 g, 20 mmol), KOH (2.24 g, 40 mmol) and 18-crown-6 (224 mg, 1.0 mmol) in benzene (100 mL) was heated at reflux for 4 h. Cooling to room temperature, concentration and purification by chromatography afforded the sub-title compound (1.59 g, 61%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. concentrationconcentration and purification by chromatography

Sources & evidence

ORD record
ord-25b53e863bfc461c80753338c3a99595
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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