Sodium Carbonate → 4-Fluoro-3'-methoxy-3-nitrobiphenyl

HRID 429107

Reaktionsgleichung

Reaktionsgleichung von HRID 429107
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:18][C:17]=1[N+:19]([O-:21])=[O:20]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Produkt 1

HCID 104907024-Fluoro-3'-methoxy-3-nitrobiphenylAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (0.8 g) was added to a mixture of 5 g 3-methoxyphenylboronic acid, 5 g 5-bromo-2-fluoronitrobenzene and 11 mL of 2 M sodium carbonate solution in 100 mL of toluene. The mixture was refluxed for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate was washed with saturated sodium bicarbonate and brine and then dried and concentrated to give an oily solid. The solid was chromatographed on silica gel (ethyl acetate:hexane (1:6)) to give 4.3 g (77% yield) of 4-fluoro-3′-methoxy-3-nitrobiphenyl.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with saturated sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oily solid
  7. customThe solid was chromatographed on silica gel (ethyl acetate:hexane (1:6))

Quellen und Nachweise

ORD-Eintrag
ord-1203cd2dec154eea851e086d70f83b57
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316429B1

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