ethyl 2-(4-chlorophenyl)-2-hydroxyacetate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (4-Chlorophenyl)-hydroxy-acetic acid ethyl ester (10.0 g, 46.6 mmol) in DCM (35 mL) was cannulated into a solution of [bis(2-methoxyethyl)amino]sulfur trifluoride (9.45 mL, 51.3 mmol) in DCM (35 mL) cooled at −78° C. After being stirred for 12 hours and allowed to warm to ambient temperature, the mixture was poured into saturated aqueous NaHCO3. The mixture was extracted with DCM and the organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude material was chromatographed (SiO2) using DCM as eluent to give (4-chlorophenyl)-fluoroacetic acid ethyl ester as a colorless oil (7.0 g). to warm to ambient temperature The mixture was extracted with DCM the organic extracts were dried (MgSO4) filtered concentrated in vacuo The crude material was chromatographed (SiO2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-chloromandelic acid (12.3 g, 65.9 mmol) in toluene (50 mL), EtOH (16 mL), and concentrated H2SO4 (0.1 mL) was refluxed for 12 hours while removing water using a Dean-Stark trap. The mixture was concentrated in vacuo, diluted with DCM, and washed with dilute aqueous NaHCO3. The separated DCM layer was dried (MgSO4), filtered, and concentrated in vacuo to give (4-chlorophenyl)-hydroxy-acetic acid ethyl ester as a colorless oil (10.0 g) that crystallized upon standing. while removing water using a Dean-Stark trap The mixture was concentrated in vacuo diluted with DCM washed with dilute aqueous NaHCO3 The separated DCM layer was dried (MgSO4) filtered concentrated in vacuo