تفاعل #531809

معادلة التفاعل

4-Benzyloxy-2,5-dimethoxyphenylboronic acid

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

5-Acetyl-2-trifluoromethanesulfonyloxybenzoic acid methyl ester

K2CO3

water

→

7b

المردود 115.6%

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

المردود 115.6%

المذيبات

brine

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىthe flask was flushed with Ar
2. 2
   workup.ADDITIONAbsolute ethanol (83 mL) and DME (94 mL) were added
3. 3
   درجة الحرارةthe reaction mixture refluxed for 4 h
4. 4
   درجة الحرارةAfter cooling
5. 5
   غسيلThe organic layer was washed with brine (2×50 mL)
6. 6
   استخلاصthe combined aqueous fraction was back extracted with ethyl acetate
7. 7
   أخرىThe combined organic fraction was dried
8. 8
   تركيزconcentrated
9. 9
   أخرىrecrystallized from ethyl acetate/hexanes

الإجراء التجريبي

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),

المصدر