1,4-Dibromobenzene → 4-Bromo-4'-t-butoxycarbonylaminobiphenyl

HRID 417553

Reaktionsgleichung

Reaktionsgleichung von HRID 417553
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:22]2[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 78041,4-DibromobenzeneHCID 11430Potassium CarbonateHCID 3613184(4-Boc-Aminophenyl)Boronic Acid

Produkt 1

HCID 596105344-Bromo-4'-t-butoxycarbonylaminobiphenylAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-tert-Butoxycarbonylamino-phenylboronic acid (500 mg, 2.11 mmol), 1,4-dibromo-benzene (2.00 g, 8.44 mmol) Pd(PPh3)4 (122 mg, 0.106 mmol) and a 2 M aqueous solution of potassium carbonate (4.2 mL, 8.44 mmol) were degassed in 1,2-dimethoxyethane (20 mL) for 10 min. The stirred suspension was heated to 80° C. for 3 hours then diluted with ethyl acetate (60 mL) and washed with water and brine. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by silica column chromatography (0% to 20% EtOAc/hexanes) to provide (4′-Bromo-biphenyl-4-yl)-carbamic acid tert-butyl ester (430 mg, 59%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica column chromatography (0% to 20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ea6af033290545229cea7b2145004052
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088368B2

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