Реакция #531809

Уравнение реакции

4-Benzyloxy-2,5-dimethoxyphenylboronic acid

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

5-Acetyl-2-trifluoromethanesulfonyloxybenzoic acid methyl ester

K2CO3

water

→

7b

Выход 115.6%

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

Выход 115.6%

Растворители

brine

ethyl acetate

Условия реакции

Обработка

1. 1
   Другоеthe flask was flushed with Ar
2. 2
   workup.ADDITIONAbsolute ethanol (83 mL) and DME (94 mL) were added
3. 3
   Температураthe reaction mixture refluxed for 4 h
4. 4
   ТемператураAfter cooling
5. 5
   ПромывкаThe organic layer was washed with brine (2×50 mL)
6. 6
   Экстракцияthe combined aqueous fraction was back extracted with ethyl acetate
7. 7
   ДругоеThe combined organic fraction was dried
8. 8
   Концентрированиеconcentrated
9. 9
   Другоеrecrystallized from ethyl acetate/hexanes

Методика

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),

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