HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Iodophenol → Ethyl (2R)-4-(4'-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Iodophenol | HCID 10894 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate | HCID 66577950 | — |
| Catalyst | Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II) | HCID 105144 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | Ethyl (2R)-4-(4'-hydroxybiphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanoate | HCID 66579462 | 54% |
Reaction Steps
A mixture of palladium (II) EnCat (0.1 equiv), potassium carbonate (3.0 equiv), 4-iodophenol and ethyl(2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butanoate, which may be prepared as in Preparation 8A, was heated to 80° C. in 10:1 1,4-dioxane-water to provide the title compound (54%) after purification by flash chromatography on silica gel. MS (LCMS) m/z 399.5 (M+Na). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.33 (t, J=7.13 Hz, 3H) 1.72 (s, 3H) 2.18-2.28 (m, 1H) 2.47-2.58 (m, 2H) 2.72-2.84 (m, 1H) 3.04 (s, 3H) 4.22-4.31 (m, 2H) 4.91 (s, 1H) 6.85-6.92 (m, 2H) 7.17-7.24 (m, 2H) 7.40-7.51 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853258B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-46e0039686aa4e5882feec86abbb9b47 |
| Source note | uspto-grants-2014_10 |