HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-Methanesulfonyl-5-trifluoromethyl-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Bromo-3-(methylsulfonyl)-5-(trifluoromethyl)benzene | HCID 53216986 | — |
| Reactant | HCID 178418416 | HCID 178418416 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 3-Methanesulfonyl-5-trifluoromethyl-benzoic acid methyl ester | HCID 70663251 | — |
Reaction Steps
The mixture consisting of 1-bromo-3-(methylsulfonyl)-5-(trifluoromethyl)benzene (0.20 g, 0.66 mmol, Combi-Blocks, Inc.), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (20.4 mg, 0.025 mmol, CAS RN 72287-26-4) and triethylamine (0.134 g, 0.184 mL, 1.32 mmol) in ethyl acetate (2 mL) and methanol (2 mL) was stirred at 110° C. under a 70 bar carbon monoxide atmosphere for 20 h. After cooling to room temperature silica gel was added and the brown suspension evaporated. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:ethyl acetate (100:0 to 50:50). Light brown oil (0.156 g; 83%). MS (GC_MS (EI)): m/z=282.0 [M].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748434B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-56615f05e1744d9c8afe47ae4c558c8f |
| Source note | uspto-grants-2014_06 |