5-Fluoro-2-nitrophenol → cis-4-Fluoro-2-(2-methoxy-cyclohexyloxy)-1-nitro-benzene

HRID 406020

Reaktionsgleichung

Reaktionsgleichung von HRID 406020
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([OH:20])[CH:19]=1.[CH3:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl>[F:13][C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([O:20][C@@H:27]2[CH2:28][CH2:29][CH2:30][CH2:31][C@@H:26]2[O:25][CH3:24])[CH:19]=1

Komponenten

7

Edukt 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 102911Cyclohexanol, 2-methoxy-HCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 67382391cis-4-Fluoro-2-(2-methoxy-cyclohexyloxy)-1-nitro-benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.36 ml DEAD were added to an ice-cooled solution of the 1.57 g 5-fluoro-2-nitrophenol, 1.95 ml 2-methoxycyclohexanol and 3.93 g triphenylphosphine in 30 ml THF. The reaction mixture was allowed to warm to rt overnight. The mixture was stirred additional 48 hours. Then the reaction mixture was diluted with methylene chloride and washed with 10% aq. potassium carbonate solution. The organic phase was passed through a hydrophobic frit and evaporated. Purification was achieved by silica gel column chromatography (solvent:10:1 iso-hexane: EtOAc).

Aufarbeitung

  1. washwashed with 10% aq. potassium carbonate solution
  2. customevaporated
  3. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-427f75dbc9b24be0a9dd8076790ea3f4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754079B2

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