3'-CHLOROBIPHENYL-4-YLAMINE synthesis

7synthesis methods

Product Name:3'-CHLOROBIPHENYL-4-YLAMINE
CAS Number:5748-36-7
Molecular formula:C12H10ClN
Molecular Weight:203.67

63503-60-6 Synthesis

63503-60-6
436 suppliers
$9.00/1g

106-40-1 Synthesis

106-40-1
469 suppliers
$12.00/5g

5748-36-7
28 suppliers
$342.30/1G

Yield:5748-36-7 75%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾;sodium carbonate in ethanol;water;toluene;Inert atmosphere;Reflux;Suzuki coupling;

Steps:

Biphenyl-4-ylamine (35a)

General procedure: To a stirred solution of 4-bromoaniline (0.69g, 4 mmol) in 40 mL of toluene was added Pd(Ph₃P)₄ (0.32 g, 0.28 mmol), a solution of sodium carbonate (2.54 g, 24 mmol) in water (20 mL) and a solution of phenylboronic acid (0.98 g, 8 mmol) in EtOH (20 mL) under nitrogen atmosphere. The reaction mixture was stirred vigorously under reflux overnight and cooled, water was added and the reaction mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were dried and concentrated to provide brown solid which was flash chromatographed on silica gel eluting with 30% EtOAc in hexanes to provide 0.18 g (27%) of 35a

References:

Venkatraj, Muthusamy;Messagie, Jonas;Joossens, Jurgen;Lambeir, Anne-Marie;Haemers, Achiel;Van Der Veken, Pieter;Augustyns, Koen [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 4,p. 1557 - 1568] Location in patent:supporting information; experimental part