Réaction #531809

Équation de réaction

4-Benzyloxy-2,5-dimethoxyphenylboronic acid

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

5-Acetyl-2-trifluoromethanesulfonyloxybenzoic acid methyl ester

K2CO3

water

→

7b

Rendement 115.6%

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

Rendement 115.6%

Solvants

brine

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autrethe flask was flushed with Ar
2. 2
   workup.ADDITIONAbsolute ethanol (83 mL) and DME (94 mL) were added
3. 3
   Températurethe reaction mixture refluxed for 4 h
4. 4
   TempératureAfter cooling
5. 5
   LavageThe organic layer was washed with brine (2×50 mL)
6. 6
   Extractionthe combined aqueous fraction was back extracted with ethyl acetate
7. 7
   AutreThe combined organic fraction was dried
8. 8
   Concentrationconcentrated
9. 9
   Autrerecrystallized from ethyl acetate/hexanes

Mode opératoire

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),

Source