Cornforth reagent → HCID 12096241, compound

HRID 2120097Notes

Reaction equation

HRID 2120097 reaction equation
[Br:1][C:2]1[C:10]2[S:9](=[O:12])(=[O:11])[N:8]([CH3:13])[CH:7]([OH:14])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:10]2[S:9](=[O:11])(=[O:12])[N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 12096240HCID 12096240, compound

Product 1

HCID 12096241HCID 12096241, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-2-methyl-2,3-dihydro-1,2-benzisothiazol-3-ol 1,1-dioxide (0.34 g, 1.2 mmol) in methylene chloride (20 mL), prepared according to the method described in Example 3 was added PDC (1.4 g, 3.6 mmol). The reaction mixture is stirred at ambient temperature over 6 h, filtered through a pad of Celite and concentrated under the reduced pressure. The residue was purified by flash chromatography (ethyl acetate/hexane, 1:4) to afford the desired product 7-bromo-2-methyl-1,2-benzisothiazol-3-one 1,1-dioxide (0.24 g, 72%). 1H NMR (CDCl3): δ 3.9 (s, 3H), 7.71 (t, 1H), 7.99 (d, 1H), 8.03 (d, 1H).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated under the reduced pressure
  3. customThe residue was purified by flash chromatography (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record
ord-5aecab263ed94098a4efc8c7a427caf5
Source dataset
uspto-grants-2004_02
Patent number
US06689770B2

Reaction notes

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