Chloroacetic Acid → 917226-71-2

To a suspension of NaH (9.6 g, 0.4 mol) in DMF (100 mL), a solution of 2-(4-bromophenyl)ethanol (20.1 g, 0.1 mol; see step (i) above) in DMF (100 mL) was added, at 0° C. The resulting mixture was then stirred for 45 minutes at room temperature. After cooling the reaction mixture to 0° C., a solution of chloroacetic acid (9.4 g, 0.1 mol) in DMF (50 mL) was added, and the resulting mixture was stirred at 55 to 60° C. for 3 h. The reaction was quenched by adding cold (about 0° C.) water and then acidification to pH 2.0 (by addition of 1.5 N HCl). The mixture was extracted with ethyl acetate (5×200 mL) and the combined organic layers were washed with water and brine. The sub-title compound was isolated as pale brown solid after evaporation (yield: 14 g, 54%).

1. temperatureAfter cooling the reaction mixture to 0° C.
2. stirringthe resulting mixture was stirred at 55 to 60° C. for 3 h
3. customThe reaction was quenched
4. additionby adding cold (about 0° C.) water
5. additionacidification to pH 2.0 (by addition of 1.5 N HCl)
6. extractionThe mixture was extracted with ethyl acetate (5×200 mL)
7. washthe combined organic layers were washed with water and brine

ORD record

ord-05c3d7e5311d498cbea0da8be2b9ca69

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928225B2