تفاعل #166066

معادلة التفاعل

HCl

5-benzyloxy-3-fluorophenyl bromide

4-acetoxystyrene

Et3N

→

desired product

المردود 88.0%

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

المردود 88.0%

المذيبات

EtOAc

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic layer was separated
2. 2
   غسيلwashed with water and brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated

الإجراء التجريبي

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.

المصدر