Furan → 2-(4-Fluorophenylmethyl)furan

Temperature

0 °C

To a 0° C. solution of furan (13.6 g, 0.20 mol) in a mixture of anhydrous ether (230 mL) and anhydrous THF (70 mL) under nitrogen was added a 2.5M solution of n-butyllithium in hexane (54.0 mL, 0.134 mol). The mixture was stirred at 0° C. for 1.5 hours and then transferred by cannula to a stirred -78° C. solution of 4-fluorobenzyl bromide (23.6 g, 0.125 mol) and tetrakis-(triphenylphosphine)palladium (O) (1.25 g, 0.001 mol) in anhydrous THF (200 mL). The transfer was made under nitrogen over a period of 30-40 minutes. The reaction mixture was stirred at ambient temperature overnight, saturated aqueous solution of ammonium chloride was added and the mixture extracted with ether. The ether layer was dried (MgSO4), concentrated in vacuo and the residue distilled at reduced pressure to give 2-(4-fluorophenylmethyl)furan as a colorless oil (17.89 g, 81% ). b.p. 57°-62° C. at 0.5-0.7 mm-Hg.

1. customtransferred by cannula to a stirred -78° C.
2. waitThe transfer was made under nitrogen over a period of 30-40 minutes
3. stirringThe reaction mixture was stirred at ambient temperature overnight
4. extractionthe mixture extracted with ether
5. dry with materialThe ether layer was dried (MgSO4)
6. concentrationconcentrated in vacuo
7. distillationthe residue distilled at reduced pressure

ORD record

ord-e27ba103370d43dd91c69944a80b85e4

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05616596