Sodium Iodide → 1-Bromo-4-(1-methyl-hexyloxy)-benzene

HRID 1725091Notes

Reaction equation

HRID 1725091 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[CH3:9][CH:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCCCCC.O>[Br:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH:10]([CH3:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:1][CH:2]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 160902-Bromoheptane

Product 1

HCID 200967851-Bromo-4-(1-methyl-hexyloxy)-benzeneYield 60.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

p-Bromophenol (295.52 grams (“g”), 1500.00 millimole) is dissolved in anhydrous dimethyl formamide (“DMF”) (500 milliliters) in a 2000 milliliter (“mL”) 3-necked flask equipped with mechanical stirrer and condenser, under an argon atmosphere. To this solution, (1-methyl) hexylbromide (322.38 grams, 1800.00 millimoles), sodium iodide (33.57 g, 225.00 mmol) and anhydrous potassium carbonate (621.95 g, 4500.00 mmol) are added. The resulting suspension is heated to 100° C. and stirred at that temperature for 72 hours. After cooling to room temperature, water (1000 mL) and n-hexane (300 mL) are added. The aqueous layer is separated and extracted with n-hexane (3×100 mL). The combined organic layers are washed with diluted sodium chloride solution (2×100 mL) and dried (MgSO4). The solvent is removed by rotary evaporation under reduced pressure and the residue is filtered using a SiO2 layer (10×10 cm) and n-hexane as eluent. After removal of solvent by rotary evaporation and in vacuo a colorless liquid (245.54 g, 60%) is obtained.

Workup

  1. customequipped with mechanical stirrer and condenser, under an argon atmosphere
  2. temperatureAfter cooling to room temperature
  3. customThe aqueous layer is separated
  4. extractionextracted with n-hexane (3×100 mL)
  5. washThe combined organic layers are washed with diluted sodium chloride solution (2×100 mL)
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed by rotary evaporation under reduced pressure
  8. filtrationthe residue is filtered
  9. customAfter removal of solvent
  10. customby rotary evaporation

Sources & evidence

ORD record
ord-319222f9c3444affa923372f1f7cb298
Source dataset
uspto-grants-2009_02
Patent number
US07488834B2

Reaction notes

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