Methyl 2-(4-fluorophenyl)acetate → Methyl 2-(4-fluorophenyl)-3-(4-(methylsulphonyl)phenyl)-3-oxopropanoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(4-fluorophenyl)acetate (2.35 g, 14 mmol) in THF (15 mL), at −78° C., was treated dropwise with 1 N lithium bis(trimethylsilyl)amide (14 mL, 14 mmol). After 15 minutes a suspension of 4-(methylsulphonyl)benzoyl chloride (3.3 g, 15 mmol) in THF (25 mL) was added in portions. The reaction mixture was stirred for 60 minutes at −78° C. and at 0 to 5° C. for 12 hours. The mixture was quenched with 10% citric acid, the THF removed in vacuo, and the residue triturated with hexanes to provide the desired product as a solid (yield: 3.4 g; 69%). MS (DCI-NH3) m/z 368 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ3.27 (s, 3H), 3.69 (s, 3H), 6.35 (s, 1H), 7.21 (m, 2H), 7.44 (m, 2H), 8.06 (d, J=9 Hz, 2H), 8.25 (d, J=9 Hz, 2H).

Provenance & Evidence