Water → 4-Bromo-2-chloro-1-[(3-methyl-2-buten-1-yl)oxy]benzene

HRID 402791Notes

Reaction equation

HRID 402791 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[C:4]([Cl:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 198594-Bromo-2-chlorophenolHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 667650934-Bromo-2-chloro-1-[(3-methyl-2-buten-1-yl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 4-bromo-2-chlorophenol (1.00 g, 4.82 mmol) and cesium carbonate (3.14 g, 9.64 mmol) in DMF (6.89 mL) at room temperature was added 4-bromo-2-methyl-2-butene (0.68 mL, 5.78 mmol) dropwise via a syringe. The reaction mixture was stirred at 85° C. for 1 hour before it was allowed to cool to room temperature. Water (30.0 mL) was then added and the mixture was extracted with hexane (75.0 mL, 2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-5% EtOAc/hexanes to afford the product as a colorless oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with hexane (75.0 mL, 2×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude mixture was purified by silica gel chromatography
  7. washeluting with 0-5% EtOAc/hexanes

Sources & evidence

ORD record
ord-6baf782f1c9546508b768f3d6d5d46d5
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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