Iodoethane → HCID 89649579, compound

HRID 2207627Notes

Reaction equation

HRID 2207627 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].I[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH2:11][CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 103079133-Bromo-4-methylphenol

Product 1

HCID 89649579HCID 89649579, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-bromo-4-methyl-phenol (1.2 g, 6.42 mmol) in anhydrous DMF (12 mL), was added iodoethane (1.55 mL, 19.25 mmol) and potassium carbonate (1.06 g, 7.7 mmol). The resulting mixture was left to stir at 80° C. for 18 h. It was allowed to cool to room temperature, poured into brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and filtered. The filtrate was evaporated and the crude residue was purified by silica gel chromatography (25 g SiO2) eluting with iso-hexane. Evaporation of desired fractions gave 2-bromo-4-ethoxy-1-methyl-benzene (D64) (0.7500 g, 3.4869 mmol, 54.3% yield) as colourless oil;

Workup

  1. waitThe resulting mixture was left
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. filtrationfiltered
  6. customThe filtrate was evaporated
  7. customthe crude residue was purified by silica gel chromatography (25 g SiO2)
  8. washeluting with iso-hexane
  9. customEvaporation of desired fractions

Sources & evidence

ORD record
ord-e943bc4469a24c64804a616d93d3d773
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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