Реакция #418002

Уравнение реакции

EtOAc

diisopropylamine

4-ethoxyphenylacetylene

1-bromo-4-iodo-benzene

→

desired product

1-Bromo-4-[(4-ethoxyphenyl)ethynyl]benzene

Растворители

THF

Условия реакции

Обработка

1. 1
   Промывкаthe organic layer is washed with ammonia (5%, 2×) and water (1×)
2. 2
   ДругоеThe organic layer is separated
3. 3
   Сушкаdried over magnesium sulphate
4. 4
   Другоеthe solvent is evaporated
5. 5
   ДругоеThe residue is purified by column chromatography (silicia gel; PE:EtOAc 9:1)

Методика

To 1.60 g (11.0 mmol) 4-ethoxyphenylacetylene in 40 mL THF are added 3.10 g (11.0 mmol) 1-bromo-4-iodo-benzene under argon, followed by 0.18 g (0.22 mmol) Pd(dppf)Cl2CH2Cl2 as catalyst, 0.04 g (0.22 mmol) copper(I)iodide and 3.10 mL (21.9 mmol) diisopropylamine as base. The mixture is stirred at rt for 3 h. After that time, EtOAc is added and the organic layer is washed with ammonia (5%, 2×) and water (1×). The organic layer is separated, dried over magnesium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silicia gel; PE:EtOAc 9:1) to yield the desired product.

Источник