Ammonium Chloride → HCID 86673607, compound

Participants

Reaction Conditions

Reaction Steps

Triphenyl-(3-trifluoromethyl-benzyl)-phosphonium bromide (808 mg, 1.61 mmol) is dissolved in THF (15 mL) and it is cooled down to −78° C. Then 1.6 M n-BuLi (2.0 mL, 3.2 mmol) is added and the reaction mixture is stirred for 15 min at −78° C. before it is warmed up to room temperature for 30 min. The mixture is cooled down to −78° C. again and 2-bromo-pyridine-4-carbaldehyde (300 mg, 1.61 mmol) is added. The mixture is stirred for 20 min at −78° C. before it is warmed up to room temperature for another 30 min. Saturated NH4Cl aqueous solution (20 mL) is added along with water (45 mL). The mixture is extracted with EtOAc (3×40 mL) and the organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 6%) affords 289 mg of the desired product.

Provenance & Evidence