Reaction #2320139

Reaction equation

1-iodopentane

4-Bromo-4′-hydroxybiphenyl

NaOH

→

desired product

4-bromo-4′-pentyloxybiphenyl

Solvents

H2O

Conditions

Procedure

4-Bromo-4′-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97% pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.51 mmol). The mixture was stirred at 90° C. for 3.75 h until the solids went into solution. Then, as the reaction proceeded, the desired product began to precipitate. The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C.

Source