Реакция #166066

Уравнение реакции

HCl

5-benzyloxy-3-fluorophenyl bromide

4-acetoxystyrene

Et3N

→

desired product

Выход 88.0%

4′-acetoxy-5-benzyloxy-3-fluorostilbene

Выход 88.0%

Растворители

EtOAc

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe organic layer was separated
2. 2
   Промывкаwashed with water and brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated

Методика

A mixture of 5-benzyloxy-3-fluorophenyl bromide (2.81 g, 10 mmol), Pd(OAc)2 (0.067 g, 0.3 mmol), tri-o-tolylphosphine (0.18 g, 0.6 mmol), 4-acetoxystyrene (2.03 g, 12.5 mmol), and Et3N (1.26 g, 12.5 mmol) in 20 mL dry DMF was stirred at 100° C. for 24 hours under N2. The dark mixture was distributed between EtOAc and 1N HCl. The organic layer was separated and washed with water and brine, dried over Na2SO4, filtered, and evaporated. After flash column, the desired product (3.19 g, 88%) was obtained. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.51-7.34 (m, 7H), 7.11-6.82 (m, 6H), 6.60 (dt, 1H); 13C NMR (CDCl3, 75 MHz) δ 169.66, 165.64, 162.40, 160.47, 150.58, 140.07 (d), 136.59, 134.76, 129.41, 128.91, 128.41, 128.04 (d), 127.79 (d), 122.11, 109.36 (d), 105.86 (d), 101.91 (d), 70.57, 21.37; 19F NMR (CDCl3, 282 MHz) δ −31675.70 (t); HRMS (EI+) found 362.1302 M+, calcd 362.1318 for C23H19FO3.

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