2-Bromo-1-fluoro-4-nitrobenzene → 4-Difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde

HRID 1788085

Reaktionsgleichung

Reaktionsgleichung von HRID 1788085
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[OH:12].[Br:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1F.[F-].[K+]>>[F:1][CH:2]([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[O:12][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[Br:14]

Komponenten

4

Edukt 3

HCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 522689Potassium FluorideHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Produkt 1

HCID 247582824-Difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde

Versuchsvorschrift

According to other embodiments, the present invention provides methods of preparing N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfoneamide-dibenzo[b,d]furan-1-carboxamide comprising the steps of: (a) reacting 4-difluoromethoxy-3-hydroxybenzaldehyde with 2-bromo-1-fluoro-4-nitrobenzene in a first solvent comprising potassium fluoride to produce 4-difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde; (b) cyclizing 4-difluoromethoxy-3-(4-nitro-2-bromophenoxy)benzaldehyde in a second solvent comprising a catalyst to produce 4-difluoromethoxy-8-nitro-1-formyl dibenzofuran; (c) oxidizing 4-difluoromethoxy-8-nitro-1-formyl dibenzofuran in a third solvent comprising an oxidizing agent to produce 4-difluoromethoxy-8-nitrobenzo[b,d]furan-1-carboxylic acid; (d) reacting 4-difluoromethoxy-8-nitrobenzo[b,d]furan-1-carboxylic acid in a fourth solvent comprising an inorganic acid halide, 4-amino-3,5-dichloropyridine and a first base, wherein N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide is produced; (e) reducing N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide in the presence of a reducing agent to produce N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide; and (f) reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide in a fifth solvent comprising methanesulfonyl chloride and a second base to produce N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-(methanesulfonamide) dibenzo[b,d]furan-1-carboxamide.

Aufarbeitung

  1. customthe present invention provides

Quellen und Nachweise

ORD-Eintrag
ord-22689c6094034a408671349ef7f00a54
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511150B2

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