Potassium Carbonate → 2,4-Dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether

HRID 402771Notes

Reaction equation

HRID 402771 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].Br[CH2:12][C:13]([CH3:15])=[CH2:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:14][C:13](=[CH2:12])[CH2:15][O:10][C:3]1[C:4]([CH3:9])=[CH:5][C:6]([Br:8])=[CH:7][C:2]=1[Br:1]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 118612,4-Dibromo-6-methylphenolHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 154540742,4-Dibromo-6-methylphenyl 2-methylprop-2-en-1-yl etherYield 43.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-dibromo-6-methylphenol (2.0 g, 7.5 mmol), 3-bromo-2-methylprop-1-ene (1.5 g, 11.3 mmol), K2CO3 (3.12 g, 22.6 mmol) in DMF (15 mL) was heated at 70° C. 2 hours. The reaction was then cooled to room temperature and was diluted with water and hexanes. The layers were separated and the organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with a gradient of 0-10% EtOAc/hexanes to give the title intermediate (1.05 g) as colorless liquid.

Workup

  1. custom2 hours
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on a silica gel column
  7. washeluting with a gradient of 0-10% EtOAc/hexanes

Sources & evidence

ORD record
ord-0e9d03538b2b4331bf190b522b9733b2
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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