Bromine → 3-Bromo-4-methylbenzo[d]isothiazole

HRID 502603Notes

Reaction equation

HRID 502603 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]Br>C(OCC)(=O)C>[Br:11][C:4]1[C:3]2[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:2]=2[S:1][N:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 162214682-Mercapto-6-methylbenzonitrile

Product 1

HCID 574365593-Bromo-4-methylbenzo[d]isothiazoleYield 179.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-mercapto-6-methylbenzonitrile (1.00 g, 6.71 mmol) in ethyl acetate (10 mL), bromine (1.05 g, 6.60 mmol) was added dropwise at 0° C. The reaction mixture was allowed to stir at 0° C. for 3 h. The reaction mixture was then allowed to warm to room temperature, followed by heating at reflux for 3 h. The reaction mixture was concentrated under reduced pressure. Crystallization of the crude mixture with hexanes gave 3-bromo-4-methylbenzo[d]isothiazole (2.7 g), which was carried forward without further purification. MW=228 confirmed by LC-MS, tr=6.82 min (Method E) MH+=229.

Workup

  1. temperatureto warm to room temperature
  2. temperatureby heating
  3. temperatureat reflux for 3 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customCrystallization of the crude mixture with hexanes

Sources & evidence

ORD record
ord-b497cee2fbeb4629abf81dd58a8c2ace
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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