(2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol → (2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone

HRID 222316Notes

Reaction equation

HRID 222316 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=[C:12]([O:18][CH3:19])[C:11]=2[F:20])[OH:9])=[CH:6][C:5]([Cl:21])=[CH:4][N:3]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=[C:12]([O:18][CH3:19])[C:11]=2[F:20])=[O:9])=[CH:6][C:5]([Cl:21])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 86609785(2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol

Product 1

HCID 86609786(2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2,5-dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol (11.6 g, 35.3 mmol) in CH2Cl2 (400 mL) was added MnO2 (80 g, 920 mmol). The reaction mixture was allowed to stir overnight, filtered through a pad of Celite, and concentrated to afford the title compound. LRMS (ESI) calc'd for (C15H10Cl2FNO2) [M+H]+, 326.0; found 326.0.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f8bd98ac025d45939de458ef0c8831cb
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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