Réaction #986701

Équation de réaction

5-(4-iodo-phenoxymethyl)-furan-2-carboxylic acid methyl ester

Intermediate 6

5-(4-iodo-phenoxymethyl)-furan-2-carboxylic acid methyl ester

4-methyl-phenyl-boronic acid

sodium hydroxide

→

5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid

Rendement 92.7%

Solvants

water

Conditions de réaction

Traitement

1. 1
   FiltrationThe mixture was filtered
2. 2
   Lavagethe residue was washed with water, ethyl acetate, methylene chloride, and methanol
3. 3
   Extractionextracted three times with ethyl acetate
4. 4
   LavageThe combined organic layers were washed with water and saturated brine
5. 5
   Séchagedried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated

Mode opératoire

A mixture of 5-(4-iodo-phenoxymethyl)-furan-2-carboxylic acid methyl ester (Intermediate 6; 100 mg, 0.28 mmol), 4-methyl-phenyl-boronic acid (42 mg, 0.31 mmol), sodium hydroxide (45 mg, 1.13 mmol), palladium(II) acetate (2 mg, 0.01 mmol) and water (10 mL) was heated at ˜50° C. overnight. The mixture was filtered and the residue was washed with water, ethyl acetate, methylene chloride, and methanol. The aqueous layer was acidified and extracted three times with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried (magnesium sulfate), filtered, and evaporated to give 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (80 mg, 84%) as a white solid.

Source