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

HRID 1185770

Reaktionsgleichung

Reaktionsgleichung von HRID 1185770
[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-6a3d9d090dd04062b99f976efd4e8e41
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669234B2

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