Hydrogen Peroxide → HCID 23114576, compound

HRID 2080493Notes

Reaction equation

HRID 2080493 reaction equation
[Br:1][C:2]1[C:3]([CH:10]([S:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.OO.[OH2:29].CCCCCC.C[OH:37]>C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH:10]([S:19]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)(=[O:37])=[O:29])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 962WaterHCID 8058HexaneHCID 23114603HCID 23114603, compound

Product 1

HCID 23114576HCID 23114576, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of [5-bromo-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridin-2-yl]methanol (550 mg, 1.20 mmol) in a mixture of methanol (10 ml) and ethyl acetate (10 ml) were added hexaammonium heptamolybdate tetrahydrate (100 mg) and 30% aqueous hydrogen peroxide (10 ml). The resulting mixture was stirred for 19 hours. After addition of water, the resulting mixture was extracted with ethyl acetate. The extract was washed sequentially with water, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium thiosulfate and brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, followed by recrystallization from hexane:ethyl acetate to give the title compound (506 mg, 1.04 mmol, 86%) as a white powder.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed sequentially with water
  3. customThe organic layer thus obtained
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. concentrationethyl acetate=2:1 eluate was concentrated under reduced pressure
  8. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-c0b0492e08314ce5b00b2cbccba59e58
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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