m-Chloroperbenzoic acid → 3-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine 1-oxide

HRID 1716289Notes

Reaction equation

HRID 1716289 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[C:17]([O:22][CH3:23])=[N+:18]([O-:32])[CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 685127243-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine

Product 1

HCID 685129393-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(4′-bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine (0.19 g, 0.51 mmol) from Step B and mCPBA (77% max., 0.25 g, 1.13 mmol) in dichloromethane (5 mL) was stirred at room temperature for 3 days. The reaction was diluted with dichloromethane and washed with aqueous Na2SO3 solution, 1N NaOH solution, water and brine. The organic layer was dried over anhydrous K2CO3 and filtered through Celite. The filtrate was concentrated under vacuo and the residue was purified by chromatography (silica gel, 10% MeOH/EtOAc) to give the desired product. MS: 386, 388 (M+H)+.

Workup

  1. washwashed with aqueous Na2SO3 solution, 1N NaOH solution, water and brine
  2. dry with materialThe organic layer was dried over anhydrous K2CO3
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under vacuo
  5. customthe residue was purified by chromatography (silica gel, 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-35d524410574471fafc78517b49a0945
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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