(3-((Dimethylamino)methyl)-5-fluorophenyl)methanol → 3-[(Dimethylamino)methyl]-5-fluorobenzaldehyde

Participants

Reaction Steps

To a solution of {3-[(dimethylamino)methyl]-5-fluorophenyl}methanol (0.100 g, 0.546 mmol, from Step 1) in Chloroform (3 mL) was added manganese(IV) oxide (0.145 g, 1.42 mmol) and the mixture was heated in an oil bath held at 80° C. for 7 hours, The reaction mixture was filtered, rinsing with copious CHCl3 and the solvent was removed from the filtrate in vacuo. The product of the reaction, containing approximately 50% aldehyde and 50%) unreacted alcohol was used without further purification in Step 3. H NMR (300 MHz, CDCl3): δ 9.99 (d, 1H), 7.78 (dd, 1H), 7.67 (ddd, 1H), 7.52 (ddd, 1H), 4.28 (s, 2H), 2.84 (s, 6H); LCMS (M+H)+: 182.0.

Provenance & Evidence