Potassium Carbonate → 2-Bromo-5-methylpyridine 1-oxide

HRID 1522570Notes

Reaction equation

HRID 1522570 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1C=C(Cl)C=C(C(OO)=[O:17])C=1.C([O-])([O-])=O.[K+].[K+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 131787372-Bromo-5-methylpyridine 1-oxideYield 7,630.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-methylpyridine (4 g, 2.3 mmol) in dichloromethane (500 mL) was added m-CPBA (52 g, 304 mmol) at 0° C. The reaction mixture was stirred at room temperature for 20 hours and the then the pH was adjusted to about 9 with a saturated solution of K2CO3. The organic layers were separated and concentrated to give a residue which was purified by flash silica chromatography eluted with petroleum ether/ethyl acetate (1:1) to give 2-bromo-5-methylpyridine 1-oxide (33 g; 75%). 1H NMR (CDCL3): δ ppm 8.25 (s, 1H), 8.75 (d, 1H, J=8.4 Hz), 6.95-6.94 (m, 1H), 2.30 (s, 3H).

Workup

  1. customThe organic layers were separated
  2. concentrationconcentrated
  3. customto give a residue which
  4. customwas purified by flash silica chromatography
  5. washeluted with petroleum ether/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7d3dfce78ee345d4b93013e086bf4d51
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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