反应 #531809

反应方程式

4-Benzyloxy-2,5-dimethoxyphenylboronic acid

5-Acetyl-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester

5-Acetyl-2-trifluoromethanesulfonyloxybenzoic acid methyl ester

K2CO3

water

→

7b

收率 115.6%

4-Acetyl-4′-benzyloxy-2′-methoxybiphenyl-2-carboxylic acid methyl ester

收率 115.6%

溶剂

brine

ethyl acetate

反应条件

后处理

1. 1
   其他the flask was flushed with Ar
2. 2
   workup.ADDITIONAbsolute ethanol (83 mL) and DME (94 mL) were added
3. 3
   温度the reaction mixture refluxed for 4 h
4. 4
   温度After cooling
5. 5
   洗涤The organic layer was washed with brine (2×50 mL)
6. 6
   萃取the combined aqueous fraction was back extracted with ethyl acetate
7. 7
   其他The combined organic fraction was dried
8. 8
   浓缩concentrated
9. 9
   其他recrystallized from ethyl acetate/hexanes

实验过程

4-Benzyloxy-2,5-dimethoxyphenylboronic acid 5b (4.15 g, 14.4 mmol), 5-Acetyl-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester 6 (4.69 g, 14.4 mmol) and K2CO3 (3.98 g, 28.8 mmol) were added and the flask was flushed with Ar. Absolute ethanol (83 mL) and DME (94 mL) were added followed by Pd (PPh3)4 (0.87 g, 0.785 mmol) and the reaction mixture refluxed for 4 h. After cooling, water (100 ml), ethyl acetate (100 mL) and brine (50 mL) were added. The organic layer was washed with brine (2×50 mL) and the combined aqueous fraction was back extracted with ethyl acetate. The combined organic fraction was dried, concentrated and recrystallized from ethyl acetate/hexanes to give 6.5 g (99%) of 7b as a yellow solid. 1H-NMR (400 MHz, CDCl3) dH 2.65 (3H, s, COCH3), 3.58 (3H, s, OCH3), 3.68 (3H, s, OCH3), 3.88 (3H, s, OCH3), 5.21 (21H, s, CH2Ph), 6.55 (1H, s, ArH), 6.86 (1H, s, ArH), 7.30-7.48 (6H, m, ArH+CH2Ph), 8.10 (1H, d, ArH),8.37(1H,s,ArH),

来源