m-Chloroperbenzoic acid → 3-Bromo-4-(cyclopropylmethoxy)pyridine 1-oxide

HRID 1480107Notes

Reaction equation

HRID 1480107 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][CH2:11]1.ClC1C=C(C(OO)=[O:21])C=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[N+:4]([O-:21])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 667160593-Bromo-4-(cyclopropylmethoxy)pyridine

Product 1

HCID 902047583-Bromo-4-(cyclopropylmethoxy)pyridine 1-oxideYield 89.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-Bromo-4-cyclopropylmethoxy-pyridine (Example 53a, 1 g, 4.38 mmol) in dichloromethane was added 3-Chloro-benzenecarboperoxoic acid (1.47 g, 6.58 mmol) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 250 mL dichloromethane and extracted with 75 mL of an aqueous solution 1M sodium bicarbonate. The organic layers was collected, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (954 mg, 89%) as a white solid. MS (ESI, m/z): 244.2 (M+H+).

Workup

  1. extractionextracted with 75 mL of an aqueous solution 1M sodium bicarbonate
  2. customThe organic layers was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-3f683895c4ec4e3e9c2ebb226b0419cc
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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