(4-Chlorophenyl)acetic acid → HCID 58538045, compound

Participants

Reaction Steps

A solution of 4-chlorophenylacetic acid (2.074 g, 12.15 mmol) in THF (16 mL) was added drop wise over three minutes to NaHMDS (1.0 M in THF, 33 mL, 33 mmol) at −78° C., then the solution was stirred for five minutes. A solution of methyl 2-fluoro-5-(trifluoromethyl)benzoate (1.93 ml, 12.2 mmol) in THF (16 mL) was added in portions over five minutes, then the solution was stirred at −78° C. for five hours. The solution was diluted with 2 N HCl (aq, 300 mL) then extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, then concentrated. The residue was purified by silica gel chromatography eluting with 0-50% DCM/hexanes to afford the title compound as a yellow liquid. 1H NMR (500 MHz, CDCl3): δ 8.15 (dd, J=6.5, 2.3 Hz, 1H); 7.81-7.77 (m, 1H); 7.31-7.24 (m, 3H); 7.17 (d, J=8.2 Hz, 2H); 4.27 (d, J=2.7 Hz, 2H).

Provenance & Evidence