Ethyl Acetate → 2-Bromo-4-isopropylanisole

HRID 1662766Notes

Reaction equation

HRID 1662766 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N+]([O-])([O-])=O.[NH4+].[Br:17]N1C(=O)CCC1=O.CCOC(C)=O>CC#N>[Br:17][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:9]=[CH:8][C:7]=1[O:10][CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 22985Ammonium nitrateHCID 67184N-bromobutanimideHCID 777834-Isopropylanisole

Product 1

HCID 220876782-Bromo-4-isopropylanisoleYield 99.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 20.0 g of 1-isopropyl-4-methoxy benzene, 1.07 g of ammonium nitrate, and 23.7 g of N-bromosuccinimide in MeCN (66.5 ml) was stirred at room temperature for one hour. To the reaction solution was added EtOAc and a saturated aqueous solution of NaHCO3, liquid separation was performed, and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/9, v/v) to obtain 30.4 g of the title compound.

Workup

  1. customa saturated aqueous solution of NaHCO3, liquid separation
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/9, v/v)

Sources & evidence

ORD record
ord-8464590027054288acd4b369abbbbe2c
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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