Butyl bromide → 1-Butoxy-3,5-difluorobenzene

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH3:5].[F:6][C:7]1[CH:8]=[C:9]([OH:14])[CH:10]=[C:11]([F:13])[CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:14][C:9]1[CH:8]=[C:7]([F:6])[CH:12]=[C:11]([F:13])[CH:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

Procedure

A solution of 1-bromobutane (11.0 g, 0.08 mol) in acetone (30 ml) was added dropwise to a stirred, refluxing mixture of 3,5-difluorophenol (9.1 g, 0.07 mol) and potassium carbonate (30 g, 0.2 mol) in acetone (200 ml). The stirred mixture was heated under reflux for 24 h (glc analysis revealed absence of starting material). The product was extracted into ether (twice), and the combined ethereal extracts were washed with water, 5% sodium hydroxide, water and dried (MgSO4). Most of the solvent was removed in vacuo, and after the removal of the final amount of solvent and the excess of 1-bromobutane at atmospheric pressure, the residue was distilled to yield a colourless liquid.