Reaction #2186218

Reaction equation

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

tri-n-butylstannylthiophene

water

→

oil

Yield 44.4%

2-[4-(1-Methyl-hexyloxy)-phenyl]-thiophene

Yield 44.4%

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature the mixture
2. 2
   ExtractionExtraction with n-hexane (3×300 mL)
3. 3
   Otherresults in two layers
4. 4
   OtherThe organic layers are separated
5. 5
   Washwashed with diluted sodium chloride solution (2×400 mL)
6. 6
   Dryingdried (MgSO4)
7. 7
   OtherAfter removal of solvent
8. 8
   Otherby rotary evaporation most of the byproducts
9. 9
   Otherare removed by distillation (p=10−3 millibar, maximum temperature Tmax=130° C.)
10. 10
    FiltrationThe residue is subjected to filtration
11. 11
    OtherAfter removal of solvent

Procedure

Tetrakistriphenylphosphinpalladium(0), (20.45 g, 17.70 mmol) is suspended in anhydrous DMF (400 mL) in a 2000 mL 3-necked flask with magnetic stirrer and condenser under an argon atmosphere. To this, 1-bromo-4-(1-methyl-hexyloxy)-benzene (240.00 g, 884.96 mmol) and tri-n-butylstannylthiophene (330.24 g, 884.96 mmol) are added. The resulting solution is stirred at 100° C. for 68 hours. After cooling to room temperature the mixture is poured into water (2000 mL) and divided into two portions of the same volume. Extraction with n-hexane (3×300 mL) results in two layers and an emulsion between those two layers. The organic layers are separated, combined, washed with diluted sodium chloride solution (2×400 mL) and dried (MgSO4). After removal of solvent by rotary evaporation most of the byproducts are removed by distillation (p=10−3 millibar, maximum temperature Tmax=130° C.). The residue is subjected to filtration using a layer of SiO2 (30×10 cm) and n-hexane as eluent. After removal of solvent, a yellowish oil (107.88 g, about 44%) with sufficient purity for synthetic purposes is obtained.

Source