Cesium carbonate → (NE,R)-N-[(3-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide

To a mixture of (R)-2-methylpropane-2-sulfinamide (2.4326 g, 20.07 mmol) and Cs2CO3 (9.81 g, 30.1 mmol) in DCM (50 mL) was added dropwise a solution of 3-bromobenzaldehyde (4.08 g, 22.08 mmol) in DCM (50 mL) over 10 min and the mixture stirred at ambient temperature for overnight. The reaction mixture was filtered through celite and the filter pad washed with DCM then with EtOAc. Filtrate was dried over MgSO4 and concentrated to give an oil which was purified by silica gel chromatography to give 161A (4.7626 g, 16.53 mmol, 82% yield) as an faint yellow colored oil. 1H NMR (500 MHz, CDCl3) δ 8.55 (s, 1H), 8.05 (t, J=1.8 Hz, 1H), 7.76 (dt, J=7.7, 1.2 Hz, 1H), 7.68-7.65 (m, 1H), 7.41-7.36 (m, 1H), 1.31-1.29 (m, 9H).

1. filtrationThe reaction mixture was filtered through celite
2. washthe filter pad washed with DCM
3. dry with materialFiltrate was dried over MgSO4
4. concentrationconcentrated
5. customto give an oil which
6. customwas purified by silica gel chromatography

ORD record

ord-9111d2e20b1b45e0beea383b381c5b35

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409908B2