m-Chloroperbenzoic acid → 5-Bromo-2-methylpyridin-1-ium-1-olate

HRID 74593Notes

Reaction equation

HRID 74593 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[N:17][CH:18]=1>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[N+:17]([O-:9])[CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 8171645-Bromo-2-methylpyridin-1-ium-1-olate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

39 g (0.16 mol) 3-chloroperbenzoic acid in 450 mL DCM (dried on sodium sulphate) were added dropwise within 2 h to 25 g (0.15 mol) 5-bromo-2-methylpyridine in 50 mL DCM. Then the reaction mixture was stirred for 20 h at RT and extracted with 15% potassium carbonate solution. The organic phase was dried on sodium sulphate and evaporated down.

Workup

  1. extractionextracted with 15% potassium carbonate solution
  2. customThe organic phase was dried on sodium sulphate
  3. customevaporated down

Sources & evidence

ORD record
ord-1b569edf3019470e82be611f0b8f9530
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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