Hydrochloric Acid → (4-Fluorophenyl)(2-thienyl)methanol

Participants

Reaction Steps

To a stirred Grignard complex, previously prepared from 17.5 g (0.10 mol) 1-bromo-4-fluorobenzene and 2.43 g (0.10 mol) magnesium turnings in 50 ml tetrahydrofuran, 8.97 g (0.080 mol) thiophene-2-carboxaldehyde, dissolved in 30 ml tetrahydrofuran, was added dropwise. Upon complete addition the reaction mixture was refluxed for 1 h and then poured on a mixture of ice and 6N hydrochloric acid. Subsequent extraction with toluene, washing of the organic layer and evaporation in vacuo, gave 18 g of the desired (4-fluorophenyl)(2-thienyl)methanol as a brown oil. This was directly converted to the corresponding (4-fluorophenyl)(2-thienyl)methyl chloride with thionyl chloride by a procedure known to the art.

Provenance & Evidence