Reaktion #166985

Reaktionsgleichung

4-tert-Butoxycarbonylamino-phenylboronic acid

1,4-dibromo-benzene

potassium carbonate

→

(4′-Bromo-biphenyl-4-yl)-carbamic acid tert-butyl ester

Ausbeute 59.0%

Lösungsmittel

ethyl acetate

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water and brine
2. 2
   TrocknenThe organic phase was dried over magnesium sulfate
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was purified by silica column chromatography (0% to 20% EtOAc/hexanes)

Vorschrift

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%).

Quelle