HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 3,2',4'-Trifluoro-biphenyl-4-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Bromo-2-fluoroaniline | HCID 123050 | — |
| Reactant | 2,4-Difluorophenylboronic acid | HCID 2734334 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 3,2',4'-Trifluoro-biphenyl-4-ylamine | HCID 59318163 | 90% |
Reaction Steps
To a solution of 4-bromo-2-fluoro-phenylamine (190 mg, 1 mmol) and 2,4-difluorophenylboronic acid (240 mg, 1 mmol) in 2.5 ml of 1,2-dimethoxy-ethane was added tetrakis(triphenylphosphine)palladium(0) (110 mg, 0.1 mmol) and 0.5 ml of 2M sodium carbonate aqueous solution. The mixture was microwaved at 150° C. for 15 min. The solvents were evaporated and the residue was diluted with CH2Cl2 and filtered. The filtration was concentrated and purified on a flash chromatography column with 0-80% EtOAc/hexanes to give 3,2′,4′-trifluoro-biphenyl-4-ylamine as an off-white solid (200 mg, 90%). LRMS calcd for C12H8F3N (m/e) 223, obsd 224 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324385B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-4afd343b053f40fba807a725f8197770 |
| Source note | uspto-grants-2012_12 |