Water → 4-Bromo-3-isopropylanisole

HRID 278793Notes

Reaction equation

HRID 278793 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[CH:5]=1)([CH3:3])[CH3:2].[Br:12]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl>[Br:12][C:9]1[CH:8]=[CH:7][C:6]([O:10][CH3:11])=[CH:5][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 109316061-Isopropyl-3-methoxy-benzene2×

Product 1

HCID 117464064-Bromo-3-isopropylanisoleYield 81.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-isopropyl-3-methoxy-benzene (Intermediate 142, 3.50 g, 23.3 mmols), molecular sieves, and silica gel in 150 mL CCl4 was treated with N-bromosuccinimide (4.98 g, 28.0 mmols) at 35° C. for 18 hours. An additional portion of N-bromosuccinimide (830.0 mg, 4.46 mmols) was added and stirring continued for 6 hours. The mixture was cooled to room temperature, H2O was added, and the mixture was filtered to remove the solids. The mixture was extracted with E2O and the combined organic layers were washed with 10% aqueous HCl, H2O, saturated aqueous NaHCO3, and saturated NaCl before being dried (MgSO4) and concentrated under reduced pressure. Column chromatography (2.5% EtOAc-hexanes) afforded 4.34 g (81%) of the title compound as a pale-yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the solids
  3. extractionThe mixture was extracted with E2O
  4. washthe combined organic layers were washed with 10% aqueous HCl, H2O, saturated aqueous NaHCO3, and saturated NaCl
  5. dry with materialbefore being dried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f7a7999e8f649f0a0e15a8298dfb111
Source dataset
uspto-grants-2002_03
Patent number
US06359135B1

Reaction notes

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