Benzyl Chloride → 3-Fluoro-4,5-bis(phenylmethoxy)benzeneacetonitrile

Participants

Reaction Steps

Benzyl chloride (0.54 mL), 4.5 mmol) was added to a solution of 3,4-dihydroxy-5-fluorobenzylcyanide 16 (330 mg, 2 mmol), K2CO3 (620 mg, 4.5 mmol) and KI (50 mg) in DMK (10 mL). The mixture was heated at reflux for 4 h, cooled and concentrated under reduced pressure. The residue was dissolved in H2O (10 mL), and EtOAc (10 mL). The organic layer was washed with brine (2×10 mL), H2O (2×10 mL), dried with anhydrous MgSO4 and concentrated under reduced pressure to an oil. The oil was purified by flash chromatography (20% EtOAc/hexanes) to give an oil which solidified on standing. The solid was crystallized from CH2Cl2 /hexanes to give 555 mg (80%) of 12 as white needles: mp 120°-121° C.; IR (KBr) 2400 cm-1 ; 1H NMR (CDCl3) δ 7.47-7.25 (m, 10H, ArH), 6.76-6.61 (m, 2H, ArH), 5.11 (s, 4H, ArCH2), 3.63 (s, 2H, ArCH2CN); analysis calc. for C22H18FNO2 ; C, H, N.

Provenance & Evidence