تفاعل #166985

معادلة التفاعل

4-tert-Butoxycarbonylamino-phenylboronic acid

1,4-dibromo-benzene

potassium carbonate

→

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

المردود 59.0%

المذيبات

ethyl acetate

1,2-dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with water and brine
2. 2
   تجفيفThe organic phase was dried over magnesium sulfate
3. 3
   تركيزconcentrated
4. 4
   أخرىThe residue was purified by silica column chromatography (0% to 20% EtOAc/hexanes)

الإجراء التجريبي

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%).

المصدر