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

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.

1. temperaturethe mixture was heated in an oil bath
2. filtrationThe reaction mixture was filtered
3. washrinsing with copious CHCl3
4. customthe solvent was removed from the filtrate in vacuo
5. customThe product of the reaction
6. customwas used without further purification in Step 3

ORD record

ord-2bf7ec3441d4425284b5b09565ce4d44

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933085B2