m-Chloroperbenzoic acid → HCID 11436184, compound

HRID 2233901Notes

Reaction equation

HRID 2233901 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19]>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[N+:15]([O-:9])[CH:16]=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 699336Methyl 5-bromopyridine-3-carboxylate

Product 1

HCID 11436184HCID 11436184, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of mCPBA (70%, 4.46 g, 18.11 mmol) in DCM (100 ml) was added to a solution of methyl 5-bromonicotinate (3.11 g, 15.09 mmol) in DCM (100 ml). After stirring at room temperature for several hours, additional mCPBA (6.6 g, 26.77 mmol) was added (in portions) to drive the reaction to completion. After 4 days, the reaction mixture was sequentially washed with a saturated solution of sodium bicarbonate followed by water. The organic phase was dried over MgSO4, and concentrated to dryness. The crude material was purified by chromatography on silica gel using 50% EtOAc/hexanes to 100% EtOAc to give 1.16 g of the title product.

Workup

  1. customthe reaction to completion
  2. washthe reaction mixture was sequentially washed with a saturated solution of sodium bicarbonate
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by chromatography on silica gel using 50% EtOAc/hexanes to 100% EtOAc

Sources & evidence

ORD record
ord-94f6b8221adb4155a1d4cfcede8a0131
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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