N-bromobutanimide → 4-Bromo-2-isopropyl-1-methoxybenzene
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationThe reaction was concentrated in vacuo
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
- customchromatographed (5% dichloromethane/hexanes)
Sources & evidence
- ORD record
- ord-8d97fdb2355a424cbaee142aeb8bcfbe
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06194454B1
Reaction notes
Loading…