3-Fluoro-4-formylbenzonitrile

Preparation of intermediat; Reaction under NExample 8A Example 11AStep 2:; [0581] Benzyl alcohol 18 (17 g, 129 mmol) was dissolved in 300 mL of dichloromethane then treated with 33 g of celite followed by PCC (33 g, 155 mmol) resulting in a dark brown suspension which was stirred vigorously. After stirring 3 hrs the reaction was complete by TLC and was filtered through a short pad (2 in. x 5 in.) of silica gel and eluted slowly with dichloromethane. The filtrate was concentrated affording the desired aldehyde (19) as a white solid (15.62 g, 93percent). NMR (DMSO-^, 400 MHz): δ 10.38 (s, IH), δ 7.95 (t, IH), δ 7.59 (d, IH), δ 7.48 (d, IH).Example 35A 3-fluoro-4 - (hydroxymethyl) benzonitrile 1.00 g (6.62 mmol) was dissolved in 50 mL of dichloromethane, manganese oxide (IV) 9.20 g (105.9 mmol) was added. The mixture was stirred overnight at room temperature, and then filtered through a short column kijel spoken. And the solvent was distilled off under reduced pressure, the residue was purified by column chromatography was purified by (silica gel, mobile phase dichloromethane). To give the title compound 120 mg (12.1percent of theory).Example 35 4-difluoromethyl-3-{4-[2-(tetrahydropyran-4-yloxy)ethoxy]phenoxy}benzamide (35a) 3-fluoro-4-formylbenzonitrile 4-Bromo-2-fluorobenzaldehyde (3.00 g, 14.8 mmol) was dissolved in dimethylformamide (12 mL), copper cyanide (1.45 g, 16.2 mmol) was added, and the mixture was stirred under a nitrogen atmosphere at 150° C. for 18 hr. The mixture was allowed to cool, to the reaction mixture were added a solution (12 mL) of iron chloride (III) (2.64 g) in 2.0 M hydrochloric acid and water (30 mL), and the mixture was stirred at room temperature for 1 hr. The precipitate was collected by filtration, dissolved in ethyl acetate/tetrahydrofuran (2:1) (60 mL), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title object compound as a brown powder (1.54 g, yield 70percent).

Molecular Weight:149.12
XLogP3:1.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:149.027691913
Monoisotopic Mass:149.027691913
Topological Polar Surface Area:40.9
Heavy Atom Count:11
Complexity:196
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes