反応 #2186218

反応方程式

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

tri-n-butylstannylthiophene

water

→

oil

収率 44.4%

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

収率 44.4%

溶媒

DMF

反応条件

後処理

1. 1
   温度After cooling to room temperature the mixture
2. 2
   抽出Extraction with n-hexane (3×300 mL)
3. 3
   その他results in two layers
4. 4
   その他The organic layers are separated
5. 5
   洗浄washed with diluted sodium chloride solution (2×400 mL)
6. 6
   乾燥dried (MgSO4)
7. 7
   その他After removal of solvent
8. 8
   その他by rotary evaporation most of the byproducts
9. 9
   その他are removed by distillation (p=10−3 millibar, maximum temperature Tmax=130° C.)
10. 10
    ろ過The residue is subjected to filtration
11. 11
    その他After removal of solvent

実験手順

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.

出典