Methyl iodide → 2-Bromo-1-methoxy-4-(1-methylpropyl)benzene

HRID 604223Notes

Reaction equation

HRID 604223 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:10][CH3:11])[CH3:9])[CH:5]=[CH:4][C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:10][CH3:11])[CH3:9])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 166412802-Bromo-4-(sec-butyl)phenol

Product 1

HCID 666029782-Bromo-1-methoxy-4-(1-methylpropyl)benzeneYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Bromo-4-sec-butyl-phenol (1.50 g) is dissolved in N,N-dimethylformamide (10 ml) and thereto are added potassium carbonate (1.18 g) and iodomethane (1.12 g) and the mixture is stirred at room temperature overnight. Thereto are added ethyl acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→20:1) to give 2-bromo-4-sec-butyl-1-methoxy-benzene (1.58 g). NMR (CDCl3): 0.80 (3H, t), 1.20 (3H, d), 1.55 (2H, m), 2.51 (1H, m), 3.87 (3H, s), 6.82 (1H, d), 7.07 (1H, d), 7.35 (1H, s).

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→20:1)

Sources & evidence

ORD record
ord-d898a82c15a04bf0b3621e2f72a5a01d
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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