Ammonium Chloride → Methyl 3-nitro-5-phenylbenzoate

HRID 1070404

Reaktionsgleichung

Reaktionsgleichung von HRID 1070404
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:18][O:19][C:20](=[O:31])[C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23](I)[CH:22]=1.[Cl-].[NH4+]>O1CCOCC1.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>[CH3:18][O:19][C:20]([C:21]1[CH:22]=[C:23]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)=[O:31]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 7020599Methyl 3-iodo-5-nitrobenzoate

Produkt 1

HCID 69687208Methyl 3-nitro-5-phenylbenzoateAusbeute 73,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Phenylboronic acid (2.14 g, 17.59 mmol), potassium phosphate (4.50 g, 21.20 mmol), tetrakis(triphenylphosphine)palladium(0) (0.283 g, 0.24 mmol) and 3-iodo-5-nitro-benzoic acid methyl ester (3.00 g, 9.77 mmol) in dioxane (30 mL) were heated at 80° C. for 3 h. Saturated ammonium chloride was added and the product was extracted, washed with water, brine, dried over magnesium sulfate, and concentrated to dryness. Purification by chromatography gave 1.85 g of 5-nitro-biphenyl-3-carboxylic acid methyl ester, as a white solid.

Aufarbeitung

  1. extractionthe product was extracted
  2. washwashed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75a58f7a5a744f7d81693cf57fe99d4c
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903086B2

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