Hydrochloric Acid → HCID 83383259, compound

Participants

Reaction Steps

To a solution of 5-dimethylamino-2-fluorobenzonitrile (viii) (331 mg, 2.02 mmol) in dry diethyl ether (10 ml) stirred at room temperature under nitrogen, was added dropwise by syringe diisobutylaluminium hydride (2.8 ml, 1.0 M in toluene, 2.8 mmol, 1.4 eq) and stirring continued for 19.5 h. The solution was chilled in an ice-bath and methanol (1.0 ml) was added dropwise and the mixture stirred for 1 h before 1.0 M HCl (9 ml) was added and stirring continued for a further 1 h. The reaction mixture was basified with NaOH (0.4 g) then partitioned between ether (50 ml) and water (50 ml) and the aqueous layer re-extracted with ether (50 ml). The combined ether extract was washed with brine (50 ml), dried over MgSO4 and evaporated to give an orange oil (323 mg), which was subjected to column chromatography (silica gel, 30×170 mm) eluting with 100% dichloromethane, affording 5-dimethylamino-2-fluorobenzaldehyde (ix) as a bright yellow-green oil (228 mg, 68%).

Provenance & Evidence