m-Chloroperbenzoic acid → 2-(4-Fluorophenyl)-3-(methoxycarbonyl)pyridine-1-oxide

HRID 1251914Notes

Reaction equation

HRID 1251914 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:26])C=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:26])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15318001Methyl 2-(4-fluorophenyl)nicotinate

Product 1

HCID 183245012-(4-Fluorophenyl)-3-(methoxycarbonyl)pyridine-1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 2-(4-fluorophenyl)pyridin-3-carboxylate (10.5 g.) and MCPBA (12.33 g., 65%) in dichloromethane was stirred at 0° C. for 1 hour and then at ambient temperature for 2 hours. It was then washed with saturated sodium bicarbonate solution (300 ml.), dried and applied directly to a silica flash column which was eluted firstly with ethyl acetate/iso-hexane (1:1), ethyl acetate and ethyl acetate/methanol (9:1) to give 2-(4-fluorophenyl)-3-(methoxycarbonyl)pyridine-1-oxide as a white solid (10.5 g.).

Workup

  1. waitat ambient temperature for 2 hours
  2. washIt was then washed with saturated sodium bicarbonate solution (300 ml.)
  3. customdried
  4. washwas eluted firstly with ethyl acetate/iso-hexane (1:1), ethyl acetate and ethyl acetate/methanol (9:1)

Sources & evidence

ORD record
ord-5d6e61d53db14707aa6750bfcbeb21fa
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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