Bromine → HCID 57436554, compound

HRID 502561Notes

Reaction equation

HRID 502561 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][N:3]=1.[Br:11]Br>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:11][C:8]1[CH:9]=[CH:10][C:5]2[S:4][N:3]=[C:2]([Cl:1])[C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 5981903-Chloro-1,2-benzisothiazole

Product 1

HCID 57436554HCID 57436554, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

3-Chlorobenzo[d]isothiazole (10 g, 59.0 mmol) was added to a solution of bromine (3.2 mL, 62.0 mmol) and silver sulfate (19.6 g, 63.0 mmol) in sulfuric acid (200 mL). The resulting brown mixture was allowed to stir at room temperature for 2h under nitrogen. The color slowly faded to pale yellow as a white precipitate formed. The precipitate was collected by vacuum filtration and triturated with hexanes to yield 5-bromo-3-chlorobenzo[d]isothiazole as a white solid (3.8 g). 1H NMR (300 MHz, CDCl3): 8.18 (s, 1H), 7.8 (d, 1H), 7.64 ppm (d, 1H).

Workup

  1. customformed
  2. filtrationThe precipitate was collected by vacuum filtration
  3. customtriturated with hexanes

Sources & evidence

ORD record
ord-479fcf29eba34bafbc024526b6d3f38b
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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