p-Bromobenzenesulfonyl chloride → 4-bromo-N-(2-fluoro-4-methylphenyl)benzenesulfonamide

HRID 1710389Notes

Reaction equation

HRID 1710389 reaction equation
BrC1C=CC(S(N2CCC2)(=O)=O)=CC=1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.[F:26][C:27]1[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:28]=1[NH2:29]>ClCCl.C([O-])([O-])=O.[K+].[K+]>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:29][C:28]2[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:27]=2[F:26])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 679842-Fluoro-4-methylanilineHCID 72132421-((4-Bromophenyl)sulfonyl)azetidine2×

Product 1

HCID 269794184-bromo-N-(2-fluoro-4-methylphenyl)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

The title compound is analogously synthesized as described for 1-(4-bromo-benzenesulfonyl)-azetidine (compound C3) from 767 mg of 4-bromo-benzenesulfonyl chloride, 451 mg of commercially available 2-fluoro-4-methyl-aniline in 12.0 ml of dichloromethane and 6.0 ml of K2CO3 solution to yield 727 mg of the title compound as colorless, amorphous solid of m.p. 111° C. ESI-MS: 361.2/363.3 (MNH4+, 100%:87%). TLC: Rf=0.57 (neat dichloromethane).

Sources & evidence

ORD record
ord-1c6d1093e30144de95c330d34c3d33ee
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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