Sodium Hydroxide → 7-Fluoro-4-methylbenzofuran

Participants

Reaction Steps

A solution of 2-(2,2-dimethoxy-ethoxy)-1-fluoro-4-methyl-benzene (48 g) in toluene (50 ml) was added dropwise to a refluxing solution of polyphosphoric acid (100 g) in toluene (350 ml) under nitrogen. The mixture was heated under reflux for 3 h, cooled to room temperature and sodium hydroxide (2N; 800 ml) added. The mixture was extracted with ether (3×300 ml) and the combined organic extracts washed with brine (2×300 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography. Eluting with hexane gave the title compound as a pale yellow oil (14.2 g)

Provenance & Evidence