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

HRID 1294478Notes

Reaction equation

HRID 1294478 reaction equation
[Cl:1][O-].[Ca+2].Cl[O-].[F:6][C:7]([F:21])([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][C:7]([F:6])([F:20])[F:21])[CH:10]=1)[O:17][CH2:16][CH2:15][C:14]2=[O:19]

Participants

6

Reactant 2

HCID 24504Calcium hypochloriteHCID 227083508-(Trifluoromethoxy)chroman-4-one

Product 1

HCID 227083446-Chloro-8-trifluoromethoxychroman-4-oneYield 87%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of calcium hypochlorite (15.4 g, 72.4 mmol) in water:acetic acid (65:5) was added a solution of 8-trifluoromethoxychroman-4-one (4.2 g, 18.1 mmol; from 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 times) and EtOAc (once). The combined organic layer was washed with water, dried (Na2SO4) and evaporated, yielding 4.2 g (87%) of the sub-title compound.

Workup

  1. extractionextracted with ether (3 times) and EtOAc (once)
  2. washThe combined organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-23e5993776804bdb82b028fc7b5c0a03
Source dataset
uspto-grants-2007_07
Patent number
US07241757B2

Reaction notes

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