Calcium hypochlorite → 6-Chloro-8-difluoromethoxychroman-4-one

HRID 353248Notes

Reaction equation

HRID 353248 reaction equation
[Cl:1][O-].[Ca+2].Cl[O-].[F:6][CH:7]([F:20])[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][CH2:16][CH2:15][C:14]2=[O:19]>O.C(O)(=O)C.C(#N)C.O>[Cl:1][C:11]1[CH:12]=[C:13]2[C:18](=[C:9]([O:8][CH:7]([F:6])[F:20])[CH:10]=1)[O:17][CH2:16][CH2:15][C:14]2=[O:19]

Participants

6

Reactant 2

HCID 24504Calcium hypochloriteHCID 227083468-Difluoromethoxychroman-4-one

Product 1

HCID 227083496-Chloro-8-difluoromethoxychroman-4-oneYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To a solution of calcium hypochlorite (29.4 g, 137.8 mmol) in water:acetic acid (125:9.5) was added a solution of 8-difluoromethoxychroman-4-one (7.4 g, 34.6 mmol, see step (iv) above) in acetonitrile (20 mL), whereafter the reaction mixture was stirred overnight. The mixture was diluted with water and extracted with ether (3×) and with EtOAc (1×). The combined organic layers were washed with water (3×), dried (Na2SO4) and evaporated, yielding 8.0 g (93%) of the subtitle compound.

Workup

  1. extractionextracted with ether (3×) and with EtOAc (1×)
  2. washThe combined organic layers were washed with water (3×)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-8efa8896b30c49c487ad764f0aac41cd
Source dataset
uspto-grants-2004_06
Patent number
US06750243B1

Reaction notes

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