Hydrochloric Acid → HCID 19802560, compound

Participants

Reaction Steps

To a stirred Grignard complex, previously prepared from 7.80 g (0.0446 mol) 1-bromo-4-fluorobenzene and 1.10 g (0.045 mol) magnesium turnings in 50 ml tetrahydrofuran, 5.00 g (0.0446 mol) thiophene-3-carboxaldehyde, dissolved in 50 ml tetrahydrofuran, was added dropwise. Upon completion of the addition, the reaction mixture was refluxed for 1 h and then poured on a mixture of ice and 6N hydrochloric acid. Subsequent extraction with dichloromethane, washing of the organic layer with water and evaporation in vacuo, left 8.50 g of crude (4-fluorophenyl)(3-thienyl)methanol as an oil. Chromatography on silica gel (THF/n-heptane 1:2 as eluent) gave 4.4 g of the pure (4-fluorophenyl)(3-thienyl)methanol, which was directly converted to the (4-fluorophenyl) (3-thienylmethyl chloride with thionyl chloride by a known procedure.

Provenance & Evidence