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

HRID 405711Notes

Reaction equation

HRID 405711 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.[C:14]([S@:18]([NH2:20])=[O:19])([CH3:17])([CH3:16])[CH3:15]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6](/[C:8](=[N:20]\[S@@:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:19])/[CH:9]([F:11])[F:10])[CH:7]=1

Participants

3

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 548578331-(5-Bromo-2-fluorophenyl)-2,2-difluoroethanone

Product 1

HCID 88878981(NE,R)-N-[1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene]-2-methylpropane-2-sulfinamideYield 77%

Procedure

In a manner analogous to that described for the preparation of sulfinyl imine A2.1 the reaction of 1-(5-bromo-2-fluoro-phenyl)-2,2-difluoro-ethanone (CAS 1262858-97-8; WO2011009943) with (R)-tert-butylsulfinamide yielded the (R)-2-methyl-propane-2-sulfinic acid [1-(5-bromo-2-fluoro-phenyl)-2,2-difluoro-eth-(E)-ylidene]-amide (77% of theory) as a yellow oil. MS (ISP): m/z=356.1 [M+H]+and 358.0 [M+2+H]+.

Sources & evidence

ORD record
ord-f1b21af795054e839499fab0ed6aaf35
Source dataset
uspto-grants-2014_06
Patent number
US08754075B2

Reaction notes

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