Ammonium Chloride → Methyl 2-amino-5-phenylbenzoate

HRID 1070392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1070392
[NH2:1][C:2]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[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>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 736224Methyl 2-amino-5-bromobenzoate

Produkt 1

HCID 16768797Methyl 2-amino-5-phenylbenzoateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in dioxane (40 mL) were added phenylboronic acid (1.91 g, 15.7 mmol), potassium phosphate (4.08 g, 19.1 mmol) and tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) under nitrogen. The mixture was heated at 85° C. for 20 h, then cooled to 0-5° C. Aqueous ammonium chloride was added and the mixture was extracted, washed with brine, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 1.45 g of methyl 2-amino-5-phenylbenzoate.

Aufarbeitung

  1. temperaturecooled to 0-5° C
  2. extractionthe mixture was extracted
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-413eecf01edc47db99f6d12b91ff891e
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903086B2

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