Iodoethane → 1-Ethoxy-4-fluoro-5-iodo-2-methoxybenzene

HRID 1438135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1438135
[F:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([OH:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH2:12](I)[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)C>[CH2:12]([O:9][C:5]1[CH:6]=[C:7]([I:8])[C:2]([F:1])=[CH:3][C:4]=1[O:10][CH3:11])[CH3:13]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 598380024-Fluoro-5-iodo-2-methoxyphenol

Produkt 1

HCID 598380601-Ethoxy-4-fluoro-5-iodo-2-methoxybenzeneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 64C (580 mg, 2.16 mmol), ethyl iodide (0.23 mL, 2.92 mmol) and K2CO3 (598 mg, 4.32 mmol) in DMF (5.0 mL) was heated at 40° C. for 3.0 h. It was diluted with diethyl ether, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude product was purified by silica gel chromatography (EtOAc:hexanes=1:5) to give 64D (540 mg, 85% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3H) 3.82 (s, 3H) 4.01 (q, J=7.03 Hz, 2H) 6.64 (d, J=9.23 Hz, 1H) 7.09 (d, J=6.15 Hz, 1H).

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customAfter evaporation of the solvent
  4. customthe crude product was purified by silica gel chromatography (EtOAc:hexanes=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-72397c95a2a0437ca592ac062cf7da80
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07622585B2

Notizen zur Reaktion

Wird geladen…