HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (4''-Chloro-4-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Reactant | (5-Trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester | HCID 57666648 | — |
| Catalyst | Bis(tri-tert-butylphosphine)palladium(0) | HCID 2734558 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (4''-Chloro-4-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-acetic acid methyl ester | HCID 66702480 | — |
Reaction Steps
A solution of (5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (100 mg, 0.2 mmol), 4-chlorophenyl boronic acid (41 mg, 0.24 mmol), K2CO3 (2 M solution in H2O, 220 μL, 0.4 mmol) in DME (2.0 mL) was heated to 80° C. in the presence of bis(tri-t-Butylphosphine) palladium (0) (cat) for 2 hrs. The mixture was cooled to room temperature filtered, diluted with EtOAc, washed with Na2CO3, dil HCl, brine, dried (MgSO4) and evaporated under reduced pressure to give an off white solid. The residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08106236B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-a60f05894bb24b6dbb06173cde999b9b |
| Source note | uspto-grants-2012_01 |