Reaction #5314

Reaction equation

4-Fluorobenzeneethanol

1,5-dibromopentane

NaOH

→

title compound

1-[2-[(5-Bromopentyl)oxy]ethyl]-4-fluorobenzene

Solvents

H2O

Conditions

Workup

1. 1
   Extractionextracted with ER (3×200 ml)
2. 2
   Otherthe combined organic extracts were evaporated
3. 3
   OtherThe residual oil was purified by [FCS]
4. 4
   Washeluting with CX-ER (100:0→100:6)

Procedure

4-Fluorobenzeneethanol (10.0 g), 1,5-dibromopentane (29 ml), tetra-n-butylammonium hydrogen sulphate (3.2 g, 9 mmol), and aqueous 12.5 M NaOH (109 ml) were stirred vigorously at RT overnight. The mixture was diluted with H2O (400 ml), extracted with ER (3×200 ml), and the combined organic extracts were evaporated. The residual oil was purified by [FCS] eluting with CX-ER (100:0→100:6), to give the title compound as a colourless oil (14.37 g). T.l.c. (ER-CX, 19:1) Rf 0.22.

Source