Bromine → HCID 57436554, compound

HRID 502564Notes

Reaction equation

HRID 502564 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 2 h 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-ce2631fc05ba4c838ed9a7f0ec28aa9c
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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