N-bromobutanimide → 4-Bromo-2-isopropyl-1-methoxybenzene

HRID 636711Notes

Reaction equation

HRID 636711 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:11])[CH3:10].[Br:12]N1C(=O)CCC1=O>C(#N)C>[CH:9]([C:4]1[CH:5]=[C:6]([Br:12])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2706232-Isopropylanisole

Product 1

HCID 146987944-Bromo-2-isopropyl-1-methoxybenzeneYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-methoxyisopropyl-benzene (2 g) and N-bromosuccinimide (2.6 g) in acetonitrile (20 mL) was stirred at ambient temperature for 18 h. The reaction was concentrated in vacuo, slurried in carbon tetrachloride and filtered. The filtrate was concentrated in vacuo. The residue was flash chromatographed (5% dichloromethane/hexanes) to afford the title compound as an oil (2.5 g).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customchromatographed (5% dichloromethane/hexanes)

Sources & evidence

ORD record
ord-8d97fdb2355a424cbaee142aeb8bcfbe
Source dataset
uspto-grants-2001_02
Patent number
US06194454B1

Reaction notes

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