Hydrochloric Acid → HCID 53415940, compound

Participants

Reaction Steps

3-fluorophenylboronic acid (0.5 g; 3.6 mmol), bromocyclopentane (0.41 g; 2.7 mmol), potassium tert-butoxide (0.49 g; 4.3 mmol), bathophenanthroline (72 mg; 0.22 mmol), bis(1,5-cyclooctadiene)nickel(0) (30 mg; 0.11 mmol) and t-butanol (9 mL) were added sequentially to a 10-20 mL microwave reactor tube containing a stir bar. The vessel was capped, placed under nitrogen, and then subjected to the following microwave conditions: Temperature=160° C.; Time=5 minutes; Power=250 W; Cooling turned on; Absorption=High; prestir=5 s; FHT turned off. The crude reaction mixture was allowed to cool to room temperature and then acidified by the addition of aqueous hydrochloric acid (15 mL; 1N) and extracted with ethyl acetate (3×20 mL). The combined organic phases were successively washed with aqueous saturated sodium bicarbonate, aqueous saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting crude residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes to give the title product as a light red solid (0.2 g).

Provenance & Evidence