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

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).

1. stirringthe solution was stirred at −78° C. for five hours
2. extractionthen extracted twice with EtOAc
3. dry with materialThe combined organic layers were dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by silica gel chromatography
7. washeluting with 0-50% DCM/hexanes

ORD record

ord-63d6d7ea47bc4feab446d21b1fce3e8f

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318667B2