Cesium carbonate → N-(4-bromo-2-fluoro-benzyl)-2-chloro-N-isobutyl-benzenesulfonamide

HRID 1665061Notes

Reaction equation

HRID 1665061 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[C:19]([F:25])[CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C(=O)C>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:9])=[O:10])=[C:19]([F:25])[CH:18]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 84693762-chloro-N-isobutyl-benzenesulfonamide

Product 1

HCID 67441654N-(4-bromo-2-fluoro-benzyl)-2-chloro-N-isobutyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 31374DimethylacetamideSolvent

Procedure

In analogy to example 10, step 3, 2-chloro-N-isobutyl-benzenesulfonamide was reacted with 4-bromo-2-fluorobenzyl bromide, cesium carbonate and 10 mol-% tetrabutylammonium iodide as a catalyst in N,N-dimethylacetamide to give N-(4-bromo-2-fluoro-benzyl)-2-chloro-N-isobutyl-benzenesulfonamide as a colorless oil. MS: 434.2 ([M+H]+)

Sources & evidence

ORD record
ord-eb985f803651430dad7fe50da4103203
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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