Réaction #2186217

Équation de réaction

p-Bromophenol

(1-methyl)hexylbromide

sodium iodide

potassium carbonate

→

liquid

Rendement 60.4%

1-Bromo-4-(1-methyl-hexyloxy)-benzene

Rendement 60.4%

Solvants

n-hexane

water

dimethyl formamide

Conditions de réaction

Traitement

1. 1
   Autreequipped with mechanical stirrer and condenser, under an argon atmosphere
2. 2
   TempératureAfter cooling to room temperature
3. 3
   AutreThe aqueous layer is separated
4. 4
   Extractionextracted with n-hexane (3×100 mL)
5. 5
   LavageThe combined organic layers are washed with diluted sodium chloride solution (2×100 mL)
6. 6
   Séchagedried (MgSO4)
7. 7
   AutreThe solvent is removed by rotary evaporation under reduced pressure
8. 8
   Filtrationthe residue is filtered
9. 9
   AutreAfter removal of solvent
10. 10
    Autreby rotary evaporation

Mode opératoire

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.

Source