4-(1-Hydroxyethyl)benzonitrile → HCID 57878394, compound

Participants

Reaction Steps

The product of Step A (1.47 g, 10 mmol) was dissolved in THF (20 mL), cooled in an ice-bath and 4-chlorophenylmagnesium bromide (21.00 mL, 21.00 mmol, 1 M in THF) was added. The reaction aged at 50° C. for 4 h and then cooled to rt overnight. The solvent had evaporated overnight and the product was taken up in 2-methyltetrhydrofuran (20 mL) and an additional 1 eq of 4-chlorophenylmagnesium bromide was added. The reaction aged at rt for 3 h and was concentrated. The reaction was diluted with 15 mL MeOH. NaBH (378 mg, 10.00 mmol) was added and the reaction aged for 1 h. The reaction was concentrated, diluted with 2M HCl (aq) and extracted with EtOAc. The organic layer was collected, dried with Na2SO4, filtered and concentrated. The residue was purified somewhat by flash chromatography on silica gel gradient eluted with 0-10% MeOH/EtOAc affording title compound. HPLC/MS: 244.9 (M—NH2)+; Rt=2.09 min

Provenance & Evidence