Bis(2-chloroethyl) ether → 4-(3-Fluorophenyl)oxane-4-carbonitrile

Participants

Reaction Steps

Potassium tert-butoxide (5.48 g, 48.8 mmol) was added to a stirred solution of 2-(3-fluorophenyl)acetonitrile (2.58 mL, 22.2 mmol) in DMF (30 mL) at 0° C. under a nitrogen atmosphere. The mixture was stirred for 10 minutes at 0° C. before 1-chloro-2-(2-chloroethoxy)ethane (2.86 mL, 24.4 mmol) was added dropwise via syringe. The reaction mixture was allowed to warm to room temperature and stirred for 6 hours. The reaction mixture was then cooled to 0° C. and quenched with 10% HCl. The aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to give the product as an orange oil (7.53 g).

Provenance & Evidence