tert-Butylsulfinamide, (R)-(+)- → (NE,R)-N-[(4-bromo-2,5-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 57426

Reaction equation

[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]([S@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>S([O-])([O-])(=O)=O.[Cu+2].ClCCCl>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5](/[CH:6]=[N:18]/[S@@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])=[C:4]([F:11])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a round bottom flask with stir bar was added 4-bromo-2,5-difluorobenzaldehyde (5.3 g, 24.0 mmol), (R)-2-methylpropane-2-sulfinamide (3.2 g, 26.4 mmol) and DCE (80 mL). To this mixture was then added copper (II) sulfate (5.74 g, 36.0 mmol). The reaction mixture was heated in a preheated oil bath at 60° C. for 18 hours. The reaction mixture was filtered through a pad celite, washing the solids with DCE. The filtrate was concentrated to afford a viscous green oil of (R,E)-N-(4-bromo-2,5-difluorobenzylidene)-2-methylpropane-2-sulfinamide (7.2 g, 22.2 mmol, 93% yield). Material was taken onto next step without further purification. LCMS m/z 326.0 (M+H)+, Rt 1.04 min.

Workup

filtrationThe reaction mixture was filtered through a pad celite
washwashing the solids with DCE
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-cab77f47765f498aa48cf0e7087220df
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434719B2

Linked notes

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