m-Chloroperbenzoic acid → HCID 86630933, compound

HRID 1696772Notes

Reaction equation

HRID 1696772 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[C:4]([Br:10])[N:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:9])=[O:19])[CH:5]=[C:4]([Br:10])[N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54276775HCID 54276775, compound

Product 1

HCID 86630933HCID 86630933, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.282 g 2,6-dibromo-4-methylsulfanyl-pyridine (Example 45a) in 5.0 ml dichlormethane was added 0.246 g m-chloroperbenzoic acid at 0° C. and the mixture was then stirred at room temperature for 3 h. The reaction mixture was partitioned between 10% potassium carbonate and ethyl acetate. The phases were separated and the organic phase was washed with brine, dried over sodium sulphate and purified by chromatography on silica gel with ethyl acetate to yield 0.260 g of the title compound as white crystals melting at 98-100° C.

Workup

  1. customThe reaction mixture was partitioned between 10% potassium carbonate and ethyl acetate
  2. customThe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. custompurified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-4d5b5b2eb78f4707ae7f922cd1387540
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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