Reaction #57648

Reaction equation

3-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester

K2CO3

furan-3-boronic acid

1,2-dimethoxyethane

→

4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Yield 68.4%

Solvents

water

water

Conditions

Workup

1. 1
   TemperatureThe mixture was heated
2. 2
   Extractionwas extracted with ethyl acetate
3. 3
   ExtractionThe organic extract
4. 4
   Washwas washed with water
5. 5
   Dryingdried over sodium sulfate
6. 6
   OtherRemoval of the solvent in vacuo
7. 7
   Othergave the crude product, which
8. 8
   Otherwas purified by column chromatography

Procedure

3-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester (285 mg, 0.75 mmol) was mixed with K2CO3 (207 mg, 2.2 eq), furan-3-boronic acid (101 mg, 1.2 eq), Pd(Ph3)4 (43 mg, 0.05 eq), 3 mL of 1,2-dimethoxyethane and 0.5 mL of water. The mixture was heated and stirred in a 85° C. oil bath for 2 h. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic extract was washed with water and dried over sodium sulfate. Removal of the solvent in vacuo gave the crude product, which was purified by column chromatography to give 153 mg of 4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester, obtained as white solid.

Source