Reacción #531809

Ecuación de reacción

4-Benzyloxy-2,5-dimethoxyphenylboronic acid

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

5-Acetyl-2-trifluoromethanesulfonyloxybenzoic acid methyl ester

K2CO3

water

→

7b

Rendimiento 115.6%

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

Rendimiento 115.6%

Disolventes

brine

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe flask was flushed with Ar
2. 2
   workup.ADDITIONAbsolute ethanol (83 mL) and DME (94 mL) were added
3. 3
   Temperaturathe reaction mixture refluxed for 4 h
4. 4
   TemperaturaAfter cooling
5. 5
   LavadoThe organic layer was washed with brine (2×50 mL)
6. 6
   Extracciónthe combined aqueous fraction was back extracted with ethyl acetate
7. 7
   OtroThe combined organic fraction was dried
8. 8
   Concentraciónconcentrated
9. 9
   Otrorecrystallized from ethyl acetate/hexanes

Procedimiento

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),

Fuente