4-Bromo-2-(trifluoromethyl)aniline → 5-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide

HRID 1693096Notes

Reaction equation

HRID 1693096 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[F:13][C:14]1[CH:27]=[CH:26][C:17]2[S:18][C:19]([S:22](Cl)(=[O:24])=[O:23])=[C:20]([CH3:21])[C:16]=2[CH:15]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:22]([C:19]2[S:18][C:17]3[CH:26]=[CH:27][C:14]([F:13])=[CH:15][C:16]=3[C:20]=2[CH3:21])(=[O:24])=[O:23])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 679604-Bromo-2-(trifluoromethyl)anilineHCID 27745865-Fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride

Product 1

HCID 249652745-Fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amideYield 66.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice cooled solution of 4-bromo-2-(trifluoromethyl)benzenamine (CAS 445-02-3, 18 g) in pyridine (25 ml) was added 5-fluoro-3-methylbenzo[b]thiophene-2-sulphonyl chloride (CAS:404964-34-7, 2.0 g). The reaction mixture was stirred at rt for 72 h, concentrated under vacuum, and the residue was chromatographed over silica gel using heptane/chloroform as eluent to obtain 5-fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-trifluoromethyl-phenyl)-amide (2.35 g) as a colorless solid. MS (ISN): 465.9, 468.0 (M−H)−

Workup

  1. concentrationconcentrated under vacuum
  2. customthe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-7861c9ab98984207901b7f9d05da662f
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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