tert-Butylsulfinamide, (S)-(-)- → (NE,S)-N-[1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene]-2-methylpropane-2-sulfinamide

HRID 1626079Notes

Reaction equation

HRID 1626079 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([C:8](=O)[CH:9]([F:11])[F:10])[CH:7]=1.[CH3:14][C:15]([S@@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6](/[C:8](=[N:20]\[S@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH:9]([F:11])[F:10])[CH:7]=1

Participants

3

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 548578331-(5-Bromo-2-fluorophenyl)-2,2-difluoroethanone

Product 1

HCID 89183621(NE,S)-N-[1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene]-2-methylpropane-2-sulfinamideYield 78%

Procedure

Starting from 1-(5-bromo-2-fluorophenyl)-2,2-difluoroethanone and (S)-(−)-2-methyl-2-propanesulfinamide, the (S,E)-N-(1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene)-2-methylpropane-2-sulfinamide (14.49 g, 78.0% yield) was obtained as a yellow oil. MS (ISP): m/z=355.9 [M+H]+ and 357.9 [M+2+H]+.

Sources & evidence

ORD record
ord-84ca13c3146542238787518c75858b76
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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