Water → 2-(4-Fluorophenyl)furan

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.7 g HgSO4 in 40 mL of 2N H2SO4 was added 5.0 g (31 mmol) of the 3,4-epoxy-3-(4'-fluorophenyl)-1-butyne in 40 mL of absolute ethanol, dropwise. The reaction mixture was refluxed for 0.25 hour and cooled to 23° C. After addition to 50 mL of H2O, the aqueous phase was extracted twice with hexanes. The hexane layers were combined, dried (MgSO4) and concentrated under reduced pressure. Sublimation (90° C. at 0.2 mmHg) of the residue yielded 2.9 g (58%) of the 2-(4'-fluorophenyl)furan as a solid (m.p. 84°-86° C.) homogeneous by spectroscopic criteria; IR (film) 1571, 1505, 1223, 1152, 785 cm-1 ; 1HNMR (80 MHz, CDCl3) 7.5-7.0 (m, 6H), 6.65 (m, 1H).

Provenance & Evidence