m-Chloroperbenzoic acid → Pyridine, 3-bromo-5-ethoxy-, 1-oxide

HRID 576137Notes

Reaction equation

HRID 576137 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][CH3:10])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:19])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N+:4]([O-:19])[CH:5]=[C:6]([O:8][CH2:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 122934803-Bromo-5-ethoxypyridine

Product 1

HCID 53497593Pyridine, 3-bromo-5-ethoxy-, 1-oxideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-5-ethoxypyridine (53 g, 262 mmol) in DCM (200 mL) at 0° C. was slowly added m-CPBA (67.9 g, 393 mmol) over 30 min. After the resulting solution was stirred for 15 h, the mixture was washed with NaS2O3 solution and extracted with DCM (2×300 mL), dried over Na2SO4 and the organic phase was concentrated to give 3-bromo-5-ethoxypyridine 1-oxide (40 g, 165 mmol, 62.9% yield): 1H NMR (400 MHz, CD3OD) δ 8.19-8.18 (m, 1H), 8.08-8.07 (m, 1H), 7.50-7.49 (m, 1H), 4.17-4.15 (d, J=8.8 Hz, 2H), 1.43 (t, J=7.0 Hz, 3H); ES-LCMS m/z 217 (M+H).

Workup

  1. customat 0° C.
  2. customover 30 min
  3. washthe mixture was washed with NaS2O3 solution
  4. extractionextracted with DCM (2×300 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-d800b2131ed54696b244db21bf01cfaa
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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