tert-Butyl methyl ether → 2-Fluoro-4-formylbenzonitrile

Participants

Reaction Steps

A solution of 22 g of 3-fluoro-4-cyanobenzyl alcohol in 50 ml of methylene chloride is added, with stirring, to 48 g of PCC in 150 ml of methylene chloride. After one hour 300 ml of methyl tert.-butyl ether are added to the reaction mixture and the latter is filtered, with the addition of Celite. Removing the solvent and recrystallising the residue from aqueous ethanol gives 3-fluoro-4-cyanobenzaldehyde, m.p. 83°-85°, IR (cm-1): 3089, 2880, 2239, 1699, 1571, 1499, 1486, 1428, 1392, 1299, 1251, 1140, 1111, 971, 900, 839, 753; 1H-NMR (200 MHz): (ppm): 7.7-8.0 (m, 3H, aromatic), 10.1 (s, 1H, CHO).

Provenance & Evidence