P-CHLOROPHENOXYACETICACIDMETHYLESTER

To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 ml_) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 ml_, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 °C for 4 h. After consumption of the starting material (TLC, 5 percent EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 ml_) and extracted with EtOAc (2 x 100 ml_). The combined organic layer was washed with brine solution (50 ml_), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15percent ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4- chlorophenoxy)acetate (22.5 g, 96.5percent yield) as pale yellow liquid. To a solution of 4-chlorophenol (15 g, 1 16.67 mmol, 1 equiv) in DMF (100 mL) at room temperature was added anhydrous potassium carbonate (24.15 g, 175.01 mmol, 1 .5 equiv ) portionwise. After stirring for 2 minutes, methyl-2-bromoacetate (13.3 mL, 140.01 mmol, 1 .2 equiv) was added. The reaction mixture was heated at 80 °C for 4 h. After consumption of the starting material (TLC, 5 percent EtOAc in hexane), the reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layer was washed with brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated en vacuo to give the crude product. The crude product was purified by flash column chromatography (Combiflash) using a silica gel column and the product was eluted at 15percent ethyl acetate in hexane. Fractions containing product were concentrated to give methyl 2-(4-chlorophenoxy)acetate (22.5 g, 96.5percent yield) as pale yellow liquid. NMR (400 MHz, CDCIGeneral procedure: To a stirred solution of phenol (1 mmol) in DMF (3 mL) were added methyl bromoacetate (0.1 mL, 1 mmol) and KTo the obtained

Molecular Weight:200.62
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:200.0240218
Monoisotopic Mass:200.0240218
Topological Polar Surface Area:35.5
Heavy Atom Count:13
Complexity:164
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes