2-Fluoro-4-formylbenzonitrile → HCID 21706154, compound

Participants

Reaction Steps

To a solution of 4-allyl-3,5-dibromo-pyridine (as described above in Step A) (2.35 g, 8.48 mmol) in THF (100 mL) at −100° C. was added n-BuLi (8.48 mmol), and the mixture was stirred for 5 min. 2-Fluoro-4-formyl-benzonitrile (as described in Example 17, Step A) (1.39 g, 9.33 mmol) in THF (5 mL) was added dropwise via syringe. The reaction mixture was stirred at −78° C. for 1 hr, quenched with saturated NH4Cl (50 mL), and partitioned between EtOAc and saturated NaHCO3. The organic layer was washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound which was purified by chromatography on silica gel with hexane: ethyl acetate 7:3-5:5.

Provenance & Evidence