Carbon Dioxide → 3-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynoic acid

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Reaction Conditions

Reaction Steps

1.93 g (8.5 mmol) of 1-(3-fluoro-benzyloxy)-4-ethynyl-benzene is dissolved in 30 ml THF and cooled to −78° C. 5.8 ml (9.4 mmol) of a 1.6 molar solution of n-butyl lithium is slowly added under stirring. The resulting solution is stirred at −78° C. for 30 minutes. An excess of solid carbon dioxide is added and the suspension is slowly allowed to warm to RT. Water is added and the mixture is acidified by addition of aqueous 0.1 molar hydrochloric acid. Extraction with ethyl acetate yields a semi-solid residue which is triturated in diethyl ether to give 1.58 g (68%) of a colorless solid. MS (neg.ions): m/e=269.1 (M−H).

Provenance & Evidence