Ammonium cerium (IV) nitrate → 2-Chloro-5,6-dihydro-1-benzothiophen-7(4H)-one

HRID 2172547Notes

Reaction equation

HRID 2172547 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[CH:6]=1.[N+]([O-])([O-])=[O:12].[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(O)(=O)C.O.O>[Cl:1][C:2]1[S:3][C:4]2[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:5]=2[CH:6]=1

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 67815172HCID 67815172, compound

Product 1

HCID 678116122-Chloro-5,6-dihydro-1-benzothiophen-7(4H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

10.0 g (57.9 mmol) of 2-chloro-4,5,6,7-tetrahydro-1-benzothiophene are dissolved in acetic acid/water (247 ml/82 ml), 127 g (231 mmol) of ammonium cerium (IV) nitrate in water (50 ml) are added and the mixture is stirred at room temperature for 5 h. The reaction mixture is added to ice-water and extracted with dichloromethane. After washing with water, the organic phase is dried over sodium sulphate and concentrated under reduced pressure. This gives 5.60 g of 2-chloro-5,6-dihydro-1-benzothiophen-7(4H)-one.

Workup

  1. extractionextracted with dichloromethane
  2. washAfter washing with water
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62e2e4f162e646bdb90415166ccc5c22
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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