Cesium carbonate → HCID 86673860, Verbindung

To a solution of 2-fluoro-1-iodo-3-(trifluoromethoxy)benzene (25 g, 81 mmol) in dry toluene (200 mL) was added Cs2CO3 (38.7 g, 120 mmol), Pd2(dba)3 (7.42 g, 8.1 mmol), BINAP (10.8 g, 16.2 mmol) and benzhydrylideneamine (19.6 g, 108 mmol). The reaction mixture was refluxed for 8 h with stirring and then cooled to RT. The organic layer was washed with water and brine and then dried over MgSO4. After removal of solvent in vacuo, the residue was purified by column chromatography on silica gel (solvent gradient from 100% n-hexane to n-hexane/EtOAc 20:1) to afford the title compound as a pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ 7.72 (s, 1H, ArH,), 7.70 (s, 1H, ArH), 7.45-7.42 (m, 1H, ArH,), 7.37-7.33 (m, 2H, ArH), 7.25-7.17 (m, 3H, ArH), 7.06 (s, 1H, ArH), 7.05 (s, 1H, ArH,), 6.84 (t, 1H, J=8 Hz, ArH), 6.78 (t, 1H, J=8 Hz, ArH), 6.67-6.64 (m, 1H, ArH).

1. temperatureThe reaction mixture was refluxed for 8 h
2. washThe organic layer was washed with water and brine
3. dry with materialdried over MgSO4
4. customAfter removal of solvent in vacuo
5. customthe residue was purified by column chromatography on silica gel (solvent gradient from 100% n-hexane to n-hexane/EtOAc 20:1)

ORD-Eintrag

ord-077fd326a9ff4b15a9b71788d62c25e9

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09085555B2