Isopropyl iodide → 2-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene

HRID 1107278Notes

Reaction equation

HRID 1107278 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].I[CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:13]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Br:1])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

Product 1

HCID 187825712-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromo-4-nitrophenol (2.5 g; Desc. 9), 2-iodopropane (2.2 g) and potassium carbonate (5 g) were refluxed in acetone (30 ml) for 18 hours. The reaction mixture was then evaporated to dryness, and taken up in ethyl acetate/water. The organic layer was washed (water, brine), dried (MgSO4) and evaporated in vacuo. Chromatography on silica eluting with 10% ethyl acetate/hexane gave the title compound (2.8 g, 94%). 1H NMR (250 MHz, CDCl3) δ 8.46 (1H, s), 8.20 (1H, m), 6.93 (1H, m), 4.75 (1H, m), 1.42 (6H, d, J=7.5 Hz).

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. washThe organic layer was washed (water, brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-651fcd11aa734fa487d7e5208c3f6339
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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