Potassium Carbonate → HCID 68633300, compound

Temperature

90 °C

1.013 g of [(5-bromo-2-methoxyphenethyl)oxy](t-butyl)diphenyl silane, 580 mg of 3-carboxymethylboronic acid, 170 mg of tetrakistriphenyl phosphine palladium and 1.01 g of potassium carbonate were dissolved in 12 ml of toluene, and the mixture was stirred overnight at 90° C. in a nitrogen atmosphere. The reaction mixture was filtered through Celite, the filtrate was concentrated, and then the residue was dissolved in 15 ml of tetrahydrofuran. To this reaction mixture was added 5 ml of tetrabutyl ammonium fluoride solution (1M) in tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and successively washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by a silica gel column, and 197 mg methyl 3-[3-(2-hydroxyethyl)-4-methoxyphenyl]benzoic acid was obtained from a fraction eluted with hexane-ethyl acetate (2:1).

1. filtrationThe reaction mixture was filtered through Celite
2. concentrationthe filtrate was concentrated
3. dissolutionthe residue was dissolved in 15 ml of tetrahydrofuran
4. additionTo this reaction mixture was added 5 ml of tetrabutyl ammonium fluoride solution (1M) in tetrahydrofuran
5. stirringthe mixture was stirred at room temperature for 2 hours
6. additionThe reaction mixture was diluted with ethyl acetate
7. washsuccessively washed with water and brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent was removed
10. customThe residue was purified by a silica gel column

ORD record

ord-898589fccf304f22b1addb30f33a0439

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687664B2