Sodium Thiosulfate → HCID 59443055, compound

HRID 1959125Notes

Reaction equation

HRID 1959125 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[CH:16][C:17]([CH3:22])([CH3:21])[O:18]2)=[CH:13][CH:12]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[Br:7][C:16]1[C:17]([CH3:21])([CH3:22])[O:18][C:19]2[C:14]([C:15]=1[C:23]1[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=1)=[CH:13][CH:12]=[C:11]([Cl:10])[CH:20]=2

Participants

4

Reactant 2

HCID 24477Sodium ThiosulfateHCID 594429257-Chloro-4-(4-fluorophenyl)-2,2-dimethyl-2h-chromen

Product 1

HCID 59443055HCID 59443055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium bromide perbromide (1.00 g) was added to a solution of 7-chloro-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromen (a compound obtained in Reference Example 5(3); 1.00 g) in dichloromethane (15 mL) under ice-cooling and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into a 15% aqueous solution of sodium thiosulfate and extracted with ethyl acetate. The organic layer was washed successively with a saturated solution of sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/chloroform=100/0 to 95/5) to give the titled compound (1.26 g) as a colorless powder.

Workup

  1. customobtained in Reference Example 5(3)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with a saturated solution of sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/chloroform=100/0 to 95/5)

Sources & evidence

ORD record
ord-d4df6ade9bfa4737a5e50ba2ce8a0512
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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